European Journal of Chemistry 2013, 4(3), 311-328. doi:10.5155/eurjchem.4.3.311-328.815

3-Formylchromones as diverse building blocks in heterocycles synthesis


Tarik El-Sayed Ali (1,*) , Magdy Ahmed Ibrahim (2) , Nasser Mohamed El-Gohary (3) , Azza Mohamed El‐Kazak (4)

(1) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo, Egypt
(2) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo, Egypt
(3) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo, Egypt
(4) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo, Egypt
(*) Corresponding Author

Received: 29 Apr 2013, Accepted: 03 Jun 2013, Published: 30 Sep 2013

Abstract


This review covers the chemical reactivity of 3-formylchromones towards condensation reactions with a variety of carbon and nitrogen nucleophiles. Some chromone derivatives linked a variety of heterocyclic systems were prepared from the direct condensation of 3-formylchromones with heterocyclic compounds containing active methylene groups. A diverse number of fused heterocyclic systems were prepared from the reaction of 3-formylchromones with some bifunctional nucleophiles, these reactions mainly proceed via condensation with the aldehydic function followed by nucleophilic attack at C-2 position of the chromone moiety.

4_3_311_328

Keywords


Addition reactions; Ring transformation; 3-Formylchromones; Gamma-Pyrone ring opening; Condensation reaction; Carbon and nitrogen nucleophiles

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.4.3.311-328.815

Article Metrics


This Abstract was viewed 2128 times | PDF Article downloaded 959 times

Citations

/


[1]. H.A.M. Ali, Magdy A. Ibrahim
Analysis of X-ray structure, dielectric properties and AC conductivity of (4E)-2-amino-3-cyanobenzo[b]oxocin-6-one
Materials Science-Poland  34(2), 386, 2016
DOI: 10.1515/msp-2016-0044
/


[2]. Nasser M. El-Gohary, Magdy A. Ibrahim, Eslam R. El-Sawy, Noura A. Abdel-fatah
Chemical Reactivity of 4,9-Dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-Carboxaldehyde Toward Some Nucleophilic Reagents
Journal of Heterocyclic Chemistry  54(2), 1467, 2017
DOI: 10.1002/jhet.2733
/


[3]. Magdy A. Ibrahim, Nasser M. El-Gohary, Sara Said
Ring Opening Ring Closure Reactions with 3-Substituted Chromones under Nucleophilic Conditions
HETEROCYCLES  91(10), 1863, 2015
DOI: 10.3987/REV-15-824
/


[4]. Shadia A. Elsayed, Aya M. Noufal, Ahmed M. El-Hendawy
Synthesis, structural characterization and antioxidant activity of some vanadium(IV), Mo(VI)/(IV) and Ru(II) complexes of pyridoxal Schiff base derivatives
Journal of Molecular Structure  1144, 120, 2017
DOI: 10.1016/j.molstruc.2017.05.020
/


[5]. Seyada A. Aboafia, Shadia A. Elsayed, Ahmed K.A. El-Sayed, Ahmed M. El-Hendawy
New transition metal complexes of 2,4-dihydroxybenzaldehyde benzoylhydrazone Schiff base (H 2 dhbh): Synthesis, spectroscopic characterization, DNA binding/cleavage and antioxidant activity
Journal of Molecular Structure  1158, 39, 2018
DOI: 10.1016/j.molstruc.2018.01.008
/


[6]. Yoshinobu Ishikawa, Yuya Motohashi
Crystal structure of (3,5-dichloro-2-hydroxyphenyl){1-[(naphthalen-1-yl)carbonyl]-1H-pyrazol-4-yl}methanone
Acta Crystallographica Section E Structure Reports Online  70(12), 522, 2014
DOI: 10.1107/S1600536814024684
/


[7]. Shadia A. Elsayed, Ian S. Butler, Betrand Jean Claude, Sahar I. Mostafa
Synthesis, characterization and anticancer activity of 3-formylchromone benzoylhydrazone metal complexes
Transition Metal Chemistry  40(2), 179, 2015
DOI: 10.1007/s11243-014-9904-z
/


[8]. Mariya al-Rashida, Gazala Batool, Almas Sattar, Syeda Abida Ejaz, Samiullah Khan, Joanna Lecka, Jean Sévigny, Abdul Hameed, Jamshed Iqbal
2-Alkoxy-3-(sulfonylarylaminomethylene)-chroman-4-ones as potent and selective inhibitors of ectonucleotidases
European Journal of Medicinal Chemistry  115, 484, 2016
DOI: 10.1016/j.ejmech.2016.02.073
/


[9]. Iryna Savych, Syeda Abida Ejaz, Syed Jawad Ali Shah, Viktor O. Iaroshenko, Alexander Villinger, Vyacheslav Ya. Sosnovskikh, Jamshed Iqbal, Afshin Abbasi, Peter Langer
Reactions of 3-Acylchromones with Heterocyclic Ketene Aminals: One-Pot Synthesis and Phosphatase Inhibitory Activity of Fused Pyridine Derivatives
European Journal of Organic Chemistry  2017(1), 186, 2017
DOI: 10.1002/ejoc.201601138
/


[10]. Vikash Kumar, Amrita Chatterjee, Mainak Banerjee
A Mild and Efficient Route to 3-Vinylchromones in Aqueous Micellar Media
Synthetic Communications  45(20), 2364, 2015
DOI: 10.1080/00397911.2015.1084008
/


[11]. Alexey Yu. Barkov, Vladislav Yu. Korotaev, Igor B. Kutyashev, Vyacheslav Ya. Sosnovskikh
Synthesis of polyfunctionalized benzophenones via the reaction of 3-formylchromones with tertiary push–pull enamines
Tetrahedron  72(16), 2026, 2016
DOI: 10.1016/j.tet.2016.03.005
/


[12]. Sandip Gangadhar Balwe, Yeon Tae Jeong
An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction
Organic & Biomolecular Chemistry  16(8), 1287, 2018
DOI: 10.1039/C7OB02933K
/


[13]. Raquel S. G. R. Seixas, Gustavo C. Ribeiro, Samuel Guieu , Artur M. S. Silva
Sequential multicomponent synthesis of highly functionalized pyridin-2(1H)-one derivatives
ChemistrySelect  1(2), 318, 2016
DOI: 10.1002/slct.201600080
/


[14]. Magdy A. Ibrahim, Nasser M. El-Gohary
Studies on the Chemical Transformations of Simple Condensates Derived from 3-Formylchromone under Nucleophilic Conditions
HETEROCYCLES  89(2), 413, 2014
DOI: 10.3987/COM-13-12899
/


[15]. Pedro A. Cano, Alejandro Islas-Jácome, Joaquín González-Marrero, Lilian Yépez-Mulia, Fernando Calzada, Rocío Gámez-Montaño
Synthesis of 3-tetrazolylmethyl-4H-chromen-4-ones via Ugi-azide and biological evaluation against Entamoeba histolytica, Giardia lamblia and Trichomona vaginalis
Bioorganic & Medicinal Chemistry  22(4), 1370, 2014
DOI: 10.1016/j.bmc.2013.12.069
/


[16]. Magdy Ahmed Ibrahim, Tarik El-Sayed Ali, Nasser Mohamed El-Gohary, Azza Mohamed El-Kazak
ChemInform Abstract: 3-Formylchromones as Diverse Building Blocks in Heterocycles Synthesis
ChemInform  45(5), no, 2014
DOI: 10.1002/chin.201405238
/


[17]. Vyacheslav Ya. Sosnovskikh, Vladislav Yu. Korotaev, Igor B. Kutyashev, Alexey Yu. Barkov, Alexander V. Safrygin
One-pot synthesis of functionalized benzo[c]coumarins and their precursors via the reaction of 2-(polyfluoroalkyl)chromones with 4-alkyl-3-cyanocoumarins
RSC Advances  6(63), 58188, 2016
DOI: 10.1039/C6RA12492E
/


[18]. Magdy A. Ibrahim, Shimaa Abdel Halim, N. Roushdy, A.A.M. Farag, Nasser M. El-Gohary
Synthesis, DFT band structure calculations, optical and photoelectrical characterizations of the novel 5-hydroxy-4-methoxy-7-oxo-7H-furo[3,2-g]chromene-6-carbonitrile (HMOFCC)
Optical Materials  73, 290, 2017
DOI: 10.1016/j.optmat.2017.08.017
/


[19]. Kranthi G. Kishore, Unnamatla M.V. Basavanag, Alejandro Islas-Jácome, Rocío Gámez-Montaño
Synthesis of imidazo[1,2-a]pyridin-chromones by a MW assisted Groebke–Blackburn–Bienaymé process
Tetrahedron Letters  56(1), 155, 2015
DOI: 10.1016/j.tetlet.2014.11.047
/


[20]. Vyacheslav Ya. Sosnovskikh
Synthesis and chemical properties of thiochromone and its 3-substituted derivatives (review)
Chemistry of Heterocyclic Compounds  52(7), 427, 2016
DOI: 10.1007/s10593-016-1906-7
/


[21]. Magdy A. Ibrahim, A.A.M. Farag, N. Roushdy, Nasser M. El-Gohary
Synthesis and photosensitivity characterizations of 9-(6-bromo-4-oxo-4H-chromen-3-yl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-2H-xanthene-1,8-(5H,9H)-dione(BOCTTX)
Journal of Molecular Structure  1105, 370, 2016
DOI: 10.1016/j.molstruc.2015.10.060
/


[22]. M. A. Ibrahim, N. M. El-Gohary, S. S. Ibrahim, S. Said
Synthesis of Some Novel Heteroannelated Chromones by Basic Rearrangement of 6-Methylchromone-3-Carbonitrile
Chemistry of Heterocyclic Compounds  50(11), 1624, 2015
DOI: 10.1007/s10593-014-1632-y
/


[23]. Magdy A. Ibrahim, Nasser M. El-Gohary
Domino reactions between 3-(6-methylchromonyl)acrylonitrile and nucleophilic reagents
Tetrahedron  74(4), 512, 2018
DOI: 10.1016/j.tet.2017.12.030
/


References

[1]. Reynolds, G. A.; Van Allan, J. A. J. Heterocycl. Chem. 1969, 6, 375-377.
http://dx.doi.org/10.1002/jhet.5570060316

[2]. Harnisch, H. Liebigs Ann. Chem. 1973, 765, 8-14.
http://dx.doi.org/10.1002/jlac.19727650103

[3]. Nohara, A.; Umetani, T.; Sanno, Y. Tetrahedron Lett. 1973, 14, 1995-1998.
http://dx.doi.org/10.1016/S0040-4039(01)96102-7

[4]. Nohara, A.; Umetani, T.; Sanno, Y. Tetrahedron 1974, 30, 3553-3561.
http://dx.doi.org/10.1016/S0040-4020(01)97034-6

[5]. Prakash, O.; Kumar, R.; Sharma, D.; Bhardwaj, V. J. Indian Chem. Soc. 2004, 81, 888-890.

[6]. Klutchko, S.; Cohen, M. P.; Shavel J. J.; Von Standtmann, M. J. Heterocycl. Chem. 1974, 11, 183-188.
http://dx.doi.org/10.1002/jhet.5570110214

[7]. Becket, G. J. P.; Ellis, G. P. Tetrahedron Lett. 1976, 17, 719-720.
http://dx.doi.org/10.1016/S0040-4039(00)74607-7

[8]. Ellis, G. P. J. Chem. Res (S). 1978, 47-48.

[9]. El-Shaaer, H. M. E.; Prejessy, A.; Zahradik, P.; Lacova, M.; Sustekova, Z. Monatch Chem. 1993, 124, 539-548.
http://dx.doi.org/10.1007/BF00819522

[10]. Eiden, F.; Haverland, H. Arch. Pharm. 1996, 5, 29-33.

[11]. Paul, S.; Gupta, R.; Gupta, M.; Loupy, A. Synthesis 2002, 75-78.
http://dx.doi.org/10.1055/s-2002-19308

[12]. Shim, Y. S.; Kim, K. C.; Chi, D. Y.; Lee, K. H.; Cho, H. Bioorg. Med. Chem. Lett. 2003, 13, 2561-2563.
http://dx.doi.org/10.1016/S0960-894X(03)00479-7

[13]. Shrestha, S.; Hwang, S. Y.; Lee, K. H.; Cho, H. Bull. Korean Chem. Soc. 2005, 26, 1138- 1140.
http://dx.doi.org/10.5012/bkcs.2005.26.7.1138

[14]. Nandgaonkar, R. G.; Ingle, V. N. Asian J. Chem. 2005, 17, 2016-2018.

[15]. Kamotra, P.; Gupta, A.K.; Gupta, R.Indian J. Chem. B 2007, 46, 866-868.

[16]. Hatzade, K. M.; Taile, V. S.; Gaidhane, P. K.; Umare, V. D.; Haldar, A. G. M.; Ingle, N. V. Indian J. Chem. B 2009, 48, 1548-1557.

[17]. Ibrahim, S. S.; Allimony, H. A.; Abdel-Halim, A. M.; Ibrahim, M. A. Arkivoc 2009, 14, 28-38.

[18]. Patil, L. R.; Ingle, V. S.; Bondge, S. P.; Mane, R. A. Indian J. Chem. 2001, 41B, 131-134.

[19]. Shankar, M. S. S.; Reddy, R. B.; Chandra, M. G. V. P.; Reddy, Y. D. J. Indian Chem. Soc. 1989, 66, 30-35.

[20]. Tuskaev, V. A.; Oganesyan, E. T.; Mutsueva, S. K. Pharm. Chem. J. 2002, 36, 309-312.
http://dx.doi.org/10.1023/A:1020828607049

[21]. Hatzade, K. M.; Taile, V. S.; Gaidhane, P. K.; Halder, A. G. M.; Ingle, V. N. Indian J. Chem. B 2008, 47, 1260-1270.

[22]. Abass, M.; Abdel-Megid, M.; Hassan, M. Synth. Commun. 2007, 37, 329-352.
http://dx.doi.org/10.1080/00397910601033930

[23]. Abass, M.; Hassan, A. Chem. Pap. 2003, 57, 267-277.

[24]. Abdel-Megid, M.; Gabr, Y.; Awas, M. A.; Abdel-Fattah, N. M. Chem. Heterocycl. Compds. 2009, 45, 1354-1364.
http://dx.doi.org/10.1007/s10593-010-0433-1

[25]. Siddiqui, Z.N.; Musthafa, T. N. M. Tetrahedron Lett. 2011, 52, 4008-4013.
http://dx.doi.org/10.1016/j.tetlet.2011.05.118

[26]. Mustafa, T. N. M.; Siddiqui, Z. N.; Husain, F. M.; Ahmad, I. Med. Chem. Res. 2010, 19, 1473-1481.

[27]. Siddiqui, Z. N.; Asad, M.; Praveen, S. Med. Chem. Res. 2008, 17, 318-325.
http://dx.doi.org/10.1007/s00044-007-9067-y

[28]. El-Shaaer, H. M. Eur. J. Chem. 2012, 3, 51-56.
http://dx.doi.org/10.5155/eurjchem.3.1.51-56.500

[29]. Melikyan, G.; Lacova, M.; Kralova, K.; El-Shaaer, H. M.; Henselova, M.; Avetisyan, A. A. Chem. Pap. 1993, 47, 388-392.

[30]. Lacova, M.; El-Shaaer, H. M.; Loss, D.; Matulova, M.; Chovancova, J.; Furdik, M. Molecules 1998, 3, 120-131.
http://dx.doi.org/10.3390/30300120

[31]. Caujoll, R.; Baziard-Mouysset, G.; Favort, J. D.; Payard, M.; Loiseau, P. R.; Amaroush, H.; Linas, M. D.; Seguela, J. P.; Loiseau, P. M.; Bories, C.; Gayral, P. Eur. J. Med. Chem. 1993, 28, 29-35.
http://dx.doi.org/10.1016/0223-5234(93)90076-Q

[32]. Gasparova, R.; Lacova, M.; El-Shaaer, H. M.; Odlerova, Z. II Farmaco 1997, 52, 251-352.

[33]. Achaiah, G.; Jayamma, Y.; Reddy, V. M. Indian J. Heteterocycl. Chem. 1991, 1, 139-143.

[34]. Karale, B. K.; Gill, C. H.; Ganages, K. N.; Bachute, M. T.; Shingare, M. S. Indian J. Heterocycl. Chem. 1999, 9, 153-154.

[35]. Karale, B. K.; Gill, C. H.; Ganage, K. N.; Bachute, M. T.; Shingare, M. S. Indian J. Heterocycl. Chem. 2003, 12, 267-270.

[36]. Carvaiho, S. A.; Desilva, E. F.; Desouza, M. N. N.; Lourence, M. C. S.; Reckova, R. R. F. Bioorg. Med. Chem. Lett. 2008, 18, 538-541.
http://dx.doi.org/10.1016/j.bmcl.2007.11.091
PMid:18068364

[37]. Joshi, R. S.; Mandhane, P. G.; Badadhe, P. V.; Gill, C. H. Ultrason. Sonochem. 2011, 18, 735-738.
http://dx.doi.org/10.1016/j.ultsonch.2010.11.001
PMid:21112230

[38]. Nohara, A.; Kuriki, H.; Saijo, T.; Ukawa, K.; Murata, T.; Kanno, M.; Sanno, Y. J. Med. Chem. 1975, 18, 34-37.
http://dx.doi.org/10.1021/jm00235a008

[39]. Karale, B. K.; Chavan, V. P.; Hangarge, R. V.; Mane, A. S. Indian J. Heterocycl. Chem. 2001, 11, 81-82.

[40]. Halnor, V. B.; Dalvi, N. R.; Joshi, N. S.; Gill, C. H.; Karale, B. K. Indian J. Chem. B 2006, 45, 288-291.

[41]. Lacova, M.; Stankovcova, H.; Bohac, A.; Kotzianova, B. Tetrahedron 2008, 64, 9646-9653.
http://dx.doi.org/10.1016/j.tet.2008.07.032

[42]. Lacova, M.; GaSparova, R.; Kois, P.; Bohac, A.; El-Shaaer, H. M. Tetrahedron 2010, 66, 1410-1419.

[43]. Kovacikova, L.; GaSparova, R.; Bohac, A.; Durana, M.; Lacova, M. Arkivoc 2010, 11, 188-203.

[44]. Shingare, M. S.; Karale, B. K.; Gill, C. H.; Ganage, K. N.; Bachute, M. T. Indian J. Heterocycl. Chem. 1999, 9, 153-154.

[45]. Kois, P.; El-Shaaer, H. M.; Lacova, M. 6thElectronic Conference on Synthetic Organic Chemistry, ECSOC-9, September 1-30, 2005.

[46]. Nohara, A.; Umetani, T.; Sanno, Y. Jap. Patent, 1975, 7, 552067; C. A., 1976, 84, 105400t.

[47]. Nohara, A.; Kuriki, H.; Saijo, T.; Sugihara, H.; Kanno, M.; Sanno, Y. J. Med. Chem. 1977, 20, 141-145.
http://dx.doi.org/10.1021/jm00211a030

[48]. Gill, C. H.; Karale, B. K.; Dalvi, N. R. Indian J. Chem. B 2005, 44, 1522-1525.

[49]. Diwakar, S. D.; Bhagwat, S. S.; Shingare, M. S.; Gill, C. H. Bioorg. Med. Chem. Lett. 2008, 18, 4678-4681.
http://dx.doi.org/10.1016/j.bmcl.2008.07.007
PMid:18650090

[50]. Luengo, J. I.; Elliott, J. D.; Xiang, J. N. PCT. Int. Appl. Wo. 97 04, 773; C. A., 1997, 126, 225307g.

[51]. Nadiu, M. S. R.; Nadiu, R. R. Indian J. Chem. B 1997, 36, 99-100.

[52]. Prousek, J.; Jurasek, A.; Kovac, J. Coll. Czech. Chem. Commun. 1980, 45, 1704-1706.

[53]. Jones W. D.; Albrecht, W. L. J. Org. Chem. 1976, 41, 706-707.
http://dx.doi.org/10.1021/jo00866a028

[54]. Bandyophadyaya, C.; Sur, K. R.; Patra, R. J. Chem. Res. (s). 1998, 12, 802-803.

[55]. Borrell, J. I.; Teixido, J.; Schuler, E.; Michelotti, E. L. Molecular Diversity 2000, 5, 163- 166.
http://dx.doi.org/10.1023/A:1016246405906

[56]. Hangarge, R. V.; Sonwane, S. A.; Jarikote, D. V.; Shingare, M. S. Green Chem. 2001, 3, 310-312.
http://dx.doi.org/10.1039/b106871g

[57]. Chandra, K. G.; Samita, B.; Nanda, G.; Basudeb, A. J. Chem. Res(s). 1998, 178-179.

[58]. Saha, S. S.; Ghosh, T.; Tarun, G.; Bandyopadhyay, C. Synth. Commun. 2008, 38, 2429-2436.
http://dx.doi.org/10.1080/00397910802139049

[59]. Awas, M. A. A. Chem. Pap. 2006, 60, 338-347.
http://dx.doi.org/10.2478/s11696-006-0062-4

[60]. Nohara, A.; Ishiguro, T.; Sanno, Y. Tetrahedron Lett. 1974, 13, 1183-1186.
http://dx.doi.org/10.1016/S0040-4039(01)82440-0

[61]. Abdel-Rahman, A. H.; Hammouda, M. A. A.; El-Desoky, S. I. Heteroatom. Chem. 2005, 16, 20-27.
http://dx.doi.org/10.1002/hc.20048

[62]. Heber, D. Synthesis 1978, 691-692.
http://dx.doi.org/10.1055/s-1978-24860

[63]. Ghosh, C. K.; Khan, S. Synthesis 1981, 903-907.
http://dx.doi.org/10.1055/s-1981-29642

[64]. Ghosh, C. K. Heterocycles 2004, 63, 2875-2898.
http://dx.doi.org/10.3987/REV-04-586

[65]. Terzidis, M.; Tsoleridis, C. A.; Stephanidou-Stephanatou, J. Tetrahedron 2007, 63, 7828-7862.
http://dx.doi.org/10.1016/j.tet.2007.05.100

[66]. Von Harnish, H. Justus Lieb. Ann. Chem. 1972, 765, 25-33.

[67]. Copeland, R. A. B.; Day, A. R. J. Am. Chem. Soc. 1943, 65, 1072-1075.
http://dx.doi.org/10.1021/ja01246a019

[68]. Brzozowski, Z.; Saczewski, F. Eur. J. Med. Chem. Chem. 2002, 37, 709-720.
http://dx.doi.org/10.1016/S0223-5234(02)01379-X

[69]. Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2 007, 3155-3162.

[70]. Sarma, G. V. S. R.; Reddy, V. M. Indian J. Heterocycl. Chem. 1993, 3, 111-116.

[71]. Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Houghton, P. G. Synthesis 1977, 133-134.
http://dx.doi.org/10.1055/s-1977-24298

[72]. Sabitha, G.; Reddy, M. M.; Archana, B.; Yadav, J. S. Synth. Commun. 1998, 28, 573-581.
http://dx.doi.org/10.1080/00397919808005928

[73]. Plaskon, A. S.; Ryabukhin, S. V.; Volochnyuk, D. M.; Shivanyuk, A. N.; Tolmachev, A. A. Tetrahedron 2008, 64, 5933-5943.
http://dx.doi.org/10.1016/j.tet.2008.04.041

[74]. Naskar, S.; Banerjee, M.; Hazra, A.; Mondal, S.; Maity, A.; Paira, R.; Sahu, K. B.; Saha, P.; Banerjee, S.; Mondal, N. B. Tetrahedron Lett. 2011, 52, 1527-1531.
http://dx.doi.org/10.1016/j.tetlet.2011.01.141

[75]. Polyakov, V. K.; Shevtsova, R. G.; Tsukerman, S. Ukr. Khim. Zh, 1981, 47, 85-87.

[76]. Haas, G.; Stanton, J. L.; Von Sprecher, A.; Wenk, P. J. Heterocycl. Chem. 1981, 18, 607- 612.
http://dx.doi.org/10.1002/jhet.5570180334

[77]. Singh, P.; Kaur, M.; Holzer, W. Eur. J. Med. Chem. 2010, 45, 4968-4082.
http://dx.doi.org/10.1016/j.ejmech.2010.08.004
PMid:20810192

[78]. Karale, B. K.; Chavan, V. P.; Mane, A. S.; Hangarge, R. V.; Gill, C. H.; Shingare, M. S. Synth. Commun. 2002, 32, 497-503.
http://dx.doi.org/10.1081/SCC-120002395

[79]. Siddiqui, Z. N.; Musthafa, T. N. M.; Praveen, S. Med. Chem. Res. 2013, 22, 127-133.
http://dx.doi.org/10.1007/s00044-012-0013-2

[80]. Khodairy, A. J. Chinese Chem. Soc. 2007, 54, 93-102.

[81]. Shelke, S. N.; Dalvi, N. R.; Kale, S. B.; More, M. S.; Gill, C. H.; Karale B. K. Indian J. Chem. B 2007, 46, 1174-1178.

[82]. Abbas, M.; Othman, E. S.; Hassan, A. Synth. Commun. 2007, 37, 607-621.
http://dx.doi.org/10.1080/00397910601055180

[83]. Lacova, M.; GaSparova, R.; Loos, D.; Liptay, T.; Pronayova, N. Molecules 2000, 5, 167- 178.
http://dx.doi.org/10.3390/50200167

[84]. Bozdag-Dundar, O.; Evranos, B.; Das-Evcimen, N.; Sarhkaya, M.; Ertan, R. Eur. J. Med. Chem. 2008, 43, 2412-2417.
http://dx.doi.org/10.1016/j.ejmech.2008.01.004
PMid:18313804

[85]. Verspohl, E. J.; Bozdağ-Dündar, O.; Kaup, R. M.; Bauer, K.; Ertan, R. Med. Chem. Res. 2009, 18, 665-670.
http://dx.doi.org/10.1007/s00044-008-9158-4

[86]. Ibrahim, M. A.; Abdel-megid, M.; El-Gohary, N. M. J. Braz. Chem. Soc. 2011, 21, 1130- 1139.
http://dx.doi.org/10.1590/S0103-50532011000600019

[87]. GaSparova, R.; Lacova, M. Coll. Czech. Commun. 1995, 60, 1178-1183.

[88]. Franz, C.; Heinisch, G.; Holzer, W.; Mereiter, K.; Strobe, B.; Zheng, C. Heterocycles 1995, 41, 2527-2551.
http://dx.doi.org/10.3987/COM-95-7203

[89]. Shutov, R. V.; Kukline, E. V.; Ivin, B. A. Russ. J. Gen. Chem. 2009, 79, 1049-1051.
http://dx.doi.org/10.1134/S107036320905034X

[90]. Eiden, F.; Haverland, H. Arch. Pharm. 1967, 300, 806-809.
http://dx.doi.org/10.1002/ardp.19673000911

[91]. Shelke, K. F.; Sapkal, K. S. B.; Niralwad, S.; Shingate, B. B.; Shingate, M. S. Cent. Eur. J. Chem. 2010, 8, 12-18.
http://dx.doi.org/10.2478/s11532-009-0111-2

[92]. Shindalkar, S. S.; Madje, B. R.; Shingare, M. S. Indian J. Chem. B 2006, 45, 2571-2573.

[93]. Prousek, J. Coll. Czech. Chem. Commun. 1991, 56, 1361.
http://dx.doi.org/10.1135/cccc19911361

[94]. Reddy, K. V.; Rao, A. V. S. Org. Prep. Proc. Int. 1997, 29, 355-357.
http://dx.doi.org/10.1080/00304949709355212

[95]. Sosnovskikh, V. Y.; Irgashev, R. A.; Levchenko, A. A. Tetrahedron 2008, 64, 6607-6614.
http://dx.doi.org/10.1016/j.tet.2008.05.032

[96]. Teimouri, M. B. Tetrahedron 2011, 67, 1837-1843.
http://dx.doi.org/10.1016/j.tet.2011.01.033

[97]. Bandyopadhyay, C.; Sur, K. R. Indian. J. Chem. B 2000, 39, 137-140.

[98]. Ibrahim, M. A.; Hassanin, H. M.; Gabr, Y. A.; Alnamer, Y. A. Eur. J. Chem. 2010, 3, 195-199.
http://dx.doi.org/10.5155/eurjchem.1.3.195-199.91

[99]. Hassanin, H. M.; Ibrahim, M. A.; Alnamer, Y. A. Turkish J. Chem. 2012, 36, 682-699.

[100]. Fitton, A. O.; Frost, J. R.; Suschitzky, H. Tetrahedron Lett. 1975, 16, 2099-2100.
http://dx.doi.org/10.1016/S0040-4039(00)75305-6

[101]. Sigg, I.; Haas, G.; Winkler, T. Helv. Chim. Acta 1982, 65, 26.
http://dx.doi.org/10.1002/hlca.19820650128

[102]. Achaiah, C.; Reddy, V. Indian J. Pharm. Sci. 1991, 53, 253-255.

[103]. Chen, H. M.; Cao, L. H. J. Chinese Chem. Soc. 2009, 56, 1028-1034.

[104]. Kapur, A.; Kumar, K.; Singh, L.; Singh, P.; Elango, M.; Subramanian, V.; Gupta, V.; Kanwal, P.; Ishar, M. P. S. Tetrahedron 2009, 65, 4593-4603.
http://dx.doi.org/10.1016/j.tet.2009.03.076

[105]. Khan, K. M.; Ambreen, N.; Hussain, S.; Perveen, S.; Choudhary, M. I. Bioorg. Med. Chem. 2009, 17, 2983-2988.
http://dx.doi.org/10.1016/j.bmc.2009.03.020
PMid:19329330

[106]. Khan, K. M.; Ambreen, N.; Mughal, U. R.; Jalil, S.; Perveen, S.; Choudhary, M. I. Eur. J. Med. Chem. 2010, 45, 4058-4064.
http://dx.doi.org/10.1016/j.ejmech.2010.05.065
PMid:20576329

[107]. Dziewulska-Kulaczkowska, A. J. Therm. Anal. Calorim. 2012, 109, 7-15.
http://dx.doi.org/10.1007/s10973-011-1387-y

[108]. El-Shaaer, H. M.; Abdel-Aziz, S. A. A.; Hanafy, F. I.; Ali, T. E.; El-Fayomy, A. Z. Eur. J. Chem. 2011, 2, 158-162.
http://dx.doi.org/10.5155/eurjchem.2.2.158-162.381

[109]. Fitton, A. O.; Haughyo, G.; Suschitzky, H. Synthesis 1979, 337-339.
http://dx.doi.org/10.1055/s-1979-28669

[110]. Lacova, M.; Stankovicova, H.; Odlerova, Z. II Farmaco 1995, 50, 885-888.

[111]. Fitton, A. O.; Frost, J. R.; Houghton, P. G.; Suschitzky, H. J. Chem. Soc., Perkin Trans. 1 1977, 1450-1452.

[112]. El-Shaaer, H. M.; Foltinova, P.; Lacova, M.; Chovancova, J.; Stankovicova, H. II Farmaco 1998, 53, 224-232.
http://dx.doi.org/10.1016/S0014-827X(98)00015-9

[113]. Stankovicova, H.; Lacova, M.; Gaplovsky, A.; Chovancova, J.; Pronayova, N. Tetrahedron 2001, 57, 3455-3464.
http://dx.doi.org/10.1016/S0040-4020(01)00219-8

[114]. Al-Rashida, M.; Ashraf, M.; Hussain, B.; Nagra, S. A.; Abbas, G. Bioorg. Med. Chem. 2011, 19, 3367-3371.
http://dx.doi.org/10.1016/j.bmc.2011.04.040
PMid:21555223

[115]. Dziewulska-Kulaczkowska, A.; Mazur, L. J. Mol. Struct. 2011, 985, 233-244.
http://dx.doi.org/10.1016/j.molstruc.2010.10.049

[116]. Plaskon, A. S.; Ryabukhin, S. V.; Volochnyuk, D. M.; Gavrilenko, K. S.; Shivanyuk, A. N.; Tolmachev, A. A. J. Org. Chem. 2008, 73, 6010-6013.
http://dx.doi.org/10.1021/jo800950y
PMid:18593188

[117]. Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2007, 1861-1871.

[118]. Kalanithi, M.; Kodimunthiri, D.; Rajarajan, M.; Tharmaraj, P. Spectrochim. Acta A 2011, 82, 290-298.
http://dx.doi.org/10.1016/j.saa.2011.07.051
PMid:21824811

[119]. Clarke, P. D.; Fitton, A. O.; Kosmirak, M.; Suschitzky, H.; Suschitzky, J. L. J. Chem. Soc., Perkin Trans. 1 1985, 1747-1756.

[120]. Ghosh, C. K.; Ray, A.; Patra, A. J. Heterocycl. Chem. 2001, 38, 1459-1463.
http://dx.doi.org/10.1002/jhet.5570380632

[121]. Fitton, A. O.; Kosmırak, M.; Suschıtzky, H. Tetrahedron Lett. 1982, 23, 3953-3956.
http://dx.doi.org/10.1016/S0040-4039(00)87752-7

[122]. Nogueras, M.; Sanchez, A.; Cobo, J.; Low, J. N. J. Heterocycl. Chem. 2002, 49, 51-54.

[123]. Lacova, M.; Puchala, A.; Solčanyova, E.; Lac, J.; Kois, S.; Chovancova, J.; Rsala, D. Molecules 2005, 10, 809-821.
http://dx.doi.org/10.3390/10070809
PMid:18007351

[124]. Eynde, J. J. V.; Hecq, N.; Kataeva, O.; Kappe, C. O. Tetrahedron 2001, 57, 1785-1791.
http://dx.doi.org/10.1016/S0040-4020(00)01157-1

[125]. Quiroga, D.; Rengifo, A.; Insuasty, B.; Abonía, R.; Nogueras, M.; Sanchez, A. Tetrahedron Lett. 2002, 43, 9061-9063.
http://dx.doi.org/10.1016/S0040-4039(02)02316-X

[126]. Abonia, R.; Insusty, B.; Quiroga, J.; Kolshorn, H.; Meier, H. J. Heterocycl. Chem. 2001, 38, 671-674.
http://dx.doi.org/10.1002/jhet.5570380321

[127]. Kubicova, L.; Pour, M.; Lacova, M.; Kralova, K.; Chovancova, J.; Kaustova, J. 9thElectronic Conference on Synthetic Organic Chemistry, ECSOC-9, September 1-30, 2002.

[128]. Reddy, G. J.; Sabitha, M. G.; Rao, A. V. S. Synth. Commun. 1987, 17, 1851-1859.
http://dx.doi.org/10.1080/00397918708077331

[129]. Plaskon, A. S.; Ryabukhin, S. V.; Volochnyuk, D. M.; Shivanyuk, A. N.; Tolmachev, A. A. Heterocycles 2008, 75, 1765-1772.
http://dx.doi.org/10.3987/COM-08-11347

[130]. Ghosh, C. K.; Khan, S. Synthesis 1980, 9, 701-702.
http://dx.doi.org/10.1055/s-1980-29176

[131]. Reddy, G. J.; Rao, A. V. S. Curr. Sci. 1981, 50, 84-86.

[132]. Sigg, I.; Haas, G.; Winkler, T. Helv. Chim. Acta 1982, 65, 275-279.
http://dx.doi.org/10.1002/hlca.19820650128

[133]. Rihs, G.; Sigg, I.; Haas, G.; Winkler, T. Helv. Chim. Acta 1985, 68, 1933-1935.
http://dx.doi.org/10.1002/hlca.19850680717

[134]. Risitano, F.; Grassi, G.; Foti, F. J. Heterocycl. Chem. 2001, 38, 1083-1086.
http://dx.doi.org/10.1002/jhet.5570380511

[135]. Abdel-Rahman, A. H.; Khalil, A. M.; Keshk, E. M. Boll. Chim. Farm. 2001, 140, 387-396.
PMid:11822227

[136]. Grolik, J.; Zwolinski, K.; Eilmes, J.; Sieron, L. Tetrahedron 2011, 67, 2623-2632.
http://dx.doi.org/10.1016/j.tet.2011.02.010

[137]. Grolik, J.; Sieron, L.; Eilmes, J. Tetrahedron Lett. 2006, 47, 8209-8213.
http://dx.doi.org/10.1016/j.tetlet.2006.09.134

[138]. Das, B.; Holla, H.; Srinivas, Y. Tetrahedron Lett. 2007, 48, 61-64.
http://dx.doi.org/10.1016/j.tetlet.2006.11.018

[139]. Maiti, S.; Panja, S. K.; Bandyopadhyay, C. Indian J. Chem. 2009, 48B, 1447-1452.

[140]. El-Desoky, E. I.; Al-Shihry, S. S. J. Heterocycl. Chem. 2008, 45, 1855-1864.
http://dx.doi.org/10.1002/jhet.5570450648

[141]. Das, B.; Kanth, B. S.; Reddy, K. R.; Kumar, A. S. J. Heterocycl. Chem. 2008, 45, 1499- 1502.
http://dx.doi.org/10.1002/jhet.5570450542

[142]. Ali, T. E.; Ibrahim, M. A. J. Braz. Chem. Soc. 2010, 21, 1007-1016.
http://dx.doi.org/10.1590/S0103-50532010000600010

[143]. Ali, T. E.; Abdel-Aziz, S. A.; El-Shaaer, H. M.; Hanafy, F. I.; El-Fauomy, A. Z. Turk. J. Chem. 2008, 32, 365-374.

[144]. Ghosh, C. K.; Khan, S. Synthesis 1981, 719-720.
http://dx.doi.org/10.1055/s-1981-29574

[145]. Shelke, S. N.; Dalvi, N. R.; Shingare, M. S.; Gill, C. H.; Karale, B. K. Indian J. Heterocycl. Chem. 2006, 15, 403-404.

[146]. Sharad, N. S.; Sonawane, M. P.; Karale, B. K.; Gill, C. H. Nature Precedings 2009, 1, 2855-2862.

[147]. Pospisil, J.; Potacek, M. Heterocycles 2004, 63, 1165-1173.
http://dx.doi.org/10.3987/COM-03-9997

[148]. Gabbutt, C. D.; Hargrove, T. F. L.; Heron, B. M.; Jones, D.; Poyner, C.; Yildiz, E.; Horton, P. N.; Hursthouse, M. B. Tetrahedron 2006, 62, 10945-10953.
http://dx.doi.org/10.1016/j.tet.2006.08.090

[149]. Ghosh, C. K.; Mukhopdyaya, K. K. J. Indian Chem. Soc. 1978, 55, 52-55.

[150]. Ghosh, C. K.; Mukhopdyaya, K. K. J. Indian Chem. Soc. 1978, 55, 386-388.

[151]. Reddy, G. J.; Sbitha, G.; Rao, A. V. S. Indian J. Chem. B 1984, 23, 99-103.

[152]. Nawrot-Modranka, J.; Nawrot, E.; Graczyk, J. Eur. J. Med. Chem. 2006, 41, 1301-1309.
http://dx.doi.org/10.1016/j.ejmech.2006.06.004
PMid:16904795

[153]. Lazrenkow, A.; Nawrot-Modranka, J.; Brzeziska, E.; Krojewska, U. R.; Ozalski, M. Med. Chem. Res. 2012, 21, 1861-1868.
http://dx.doi.org/10.1007/s00044-011-9703-4

[154]. Ghosh, C. K.; Sinharoy, D. K.; Mukhopadhyaya, K. K. J. Chem. Soc., Perkin Trans. 1 1979, 1981-1985.

[155]. Bosinski, W.; Jerzmanowska, Z. Pol. J. Chem. 1983, 57, 471-474.

[156]. Petersen, U.; Heitzer, H. Liebigs Ann. Chem. 1976, 1663-1666.

[157]. Sosnovskikh, V. Y.; Moshkin, V. S.; Kodess, M. I.; Tetrahedron Lett. 2008, 49, 6856- 6859.
http://dx.doi.org/10.1016/j.tetlet.2008.09.091

[158]. Sosnovskikh, V. Y.; Moshkin, V. S.; Kodess, M. I. Mendeleev Commun. 2010, 20, 209- 211.
http://dx.doi.org/10.1016/j.mencom.2010.06.009

[159]. Maiti, S.; Panja, S. K.; Bandyopodhyay, C. Tetrahedron Lett. 2009, 50, 3966-3969.
http://dx.doi.org/10.1016/j.tetlet.2009.04.087

[160]. Ishar, M. P. S.; Kumar, K.; Singh, R. Tetrahedron Lett. 1998, 39, 6547-6550.
http://dx.doi.org/10.1016/S0040-4039(98)01362-8

[161]. Lowe, W. Synthesis 1976, 274-276.
http://dx.doi.org/10.1055/s-1976-24020

[162]. Ghosh, C. K.; Khan, S. C. Indian J. Chem. B 1979, 18, 128-130.

[163]. Pene, C.; Hubert-Habart, M. J. Heterocycl. Chem. 1980, 17, 61-64.
http://dx.doi.org/10.1002/jhet.5570170223

[164]. Crowther, A. F.; Curd, F. H. S.; Richardson, D. N.; Rose, F. L. J. Chem. Soc. 1984, 1636.

[165]. Borrell, J. I.; Teixido, J.; Schuler, E.; Michelotti, E. Tetrahedron Lett. 2001, 42, 5331- 5334.
http://dx.doi.org/10.1016/S0040-4039(01)00999-6

[166]. Bruno, O.; Brullo, C.; Ranis, A.; Schenone, S.; Bondavalli, F.; Barocelli, E.; Chivarini, M.; Ballabeni, V.; Impicciatore, M.; Tognolini, M. Bioorg. Med. Chem. Lett. 2011, 11, 1397-1400.
http://dx.doi.org/10.1016/S0960-894X(01)00221-9

[167]. Tsao, L.; Van, V.; Sun, G.; Lyu, Y. Russ. J. Gen. Chem. 2001, 71, 767-769.
http://dx.doi.org/10.1023/A:1012369621168

[168]. Cao, L. H.; Huang, Y. L. Y. T.; Sun, G. Z. Yingyong Huaxue 2001, 18, 312-313.

[169]. Foltinova, P.; Lacova, M.; Loss, D. II Farmaco2000, 55, 21-26.
http://dx.doi.org/10.1016/S0014-827X(99)00114-7

[170]. Cao, L.; Wang, W. Chem. Heterocycl. Compd. 2003, 39, 1072-1075.
http://dx.doi.org/10.1023/B:COHC.0000003526.98678.6e

[171]. Wang, B. D.; Yang, Z. Y.; Zhang, D. W.; Wang, Y. Spectrochim. Acta A 2006, 63, 213-219.
http://dx.doi.org/10.1016/j.saa.2005.05.007
PMid:15951232

[172]. Tsao, L.; Chzhan, L.; Lyu, T. Chem. Nat. Compd. 2001, 37, 311-314
http://dx.doi.org/10.1023/A:1013754030975

[173]. Ali, T. E.; Abdel-Aziz, S. A.; El-Shaaer, H. M.; Hanafy, F. I.; El-Fauomy, A. Z. Phosphorous, Sulfur and Silicon Rel. Elem. 2008, 183, 2139-2160.
http://dx.doi.org/10.1080/10426500701851291


How to cite


Ali, T.; Ibrahim, M.; El-Gohary, N.; El‐Kazak, A. Eur. J. Chem. 2013, 4(3), 311-328. doi:10.5155/eurjchem.4.3.311-328.815
Ali, T.; Ibrahim, M.; El-Gohary, N.; El‐Kazak, A. 3-Formylchromones as diverse building blocks in heterocycles synthesis. Eur. J. Chem. 2013, 4(3), 311-328. doi:10.5155/eurjchem.4.3.311-328.815
Ali, T., Ibrahim, M., El-Gohary, N., & El‐Kazak, A. (2013). 3-Formylchromones as diverse building blocks in heterocycles synthesis. European Journal of Chemistry, 4(3), 311-328. doi:10.5155/eurjchem.4.3.311-328.815
Ali, Tarik, Magdy Ahmed Ibrahim, Nasser Mohamed El-Gohary, & Azza Mohamed El‐Kazak. "3-Formylchromones as diverse building blocks in heterocycles synthesis." European Journal of Chemistry [Online], 4.3 (2013): 311-328. Web. 17 Jan. 2019
Ali, Tarik, Ibrahim, Magdy, El-Gohary, Nasser, AND El‐Kazak, Azza. "3-Formylchromones as diverse building blocks in heterocycles synthesis" European Journal of Chemistry [Online], Volume 4 Number 3 (30 September 2013)

DOI Link: https://doi.org/10.5155/eurjchem.4.3.311-328.815

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2018  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2018 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.