3-Formylchromones as diverse building blocks in heterocycles synthesis

Tarik El-Sayed Ali; Magdy Ahmed Ibrahim; Nasser Mohamed El-Gohary; Azza Mohamed El‐Kazak

doi:10.5155/eurjchem.4.3.311-328.815

PDF

Published: Sep 30, 2013

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

Keywords:

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

Section

Review Article

Issue

Vol. 4 No. 3 (2013): September 2013

Dates

Received 2013-04-29
Accepted 2013-06-03
Published 2013-09-30

Tarik El-Sayed Ali

Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo, Egypt

Magdy Ahmed Ibrahim

Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo, Egypt

Nasser Mohamed El-Gohary

Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo, Egypt

Azza Mohamed El‐Kazak

Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo, Egypt

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.

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Ali, T. E.-S.; Ibrahim, M. A.; El-Gohary, N. M.; El‐Kazak, A. M. 3-Formylchromones As Diverse Building Blocks in Heterocycles Synthesis. Eur. J. Chem. 2013, 4, 311-328.

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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

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