Utility of 2-cyano-3-phenyl-2-propenoyl chloride as Michael’s acceptor in heterocyclic synthesis with mono- and bi-dentate nucleophiles | European Journal of Chemistry

Default Image

PDF

Published: Jun 30, 2011

DOI: https://doi.org/10.5155/eurjchem.2.2.200-205.365

Keywords:

Mono- and bi-dentate nucleophiles, 2-propenoyl chloride, Benzoxazinone, Quinazolinone, Oxadiazole, Benzoxazole

Section

Research Article

Issue

Vol. 2 No. 2 (2011): June 2011

Dates

Received 2010-12-07
Accepted 2011-03-22
Published 2011-06-30

Sayed Ahmed Shiba

eMail

Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, 11566, Cairo, Egypt

Hassan Mohamed Fawzy Madkour

eMail

Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, 11566, Cairo, Egypt

Ashraf Ahmed Hamed

eMail

Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, 11566, Cairo, Egypt

Hatem Mohamed Sayed

eMail

Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, 11566, Cairo, Egypt

Maher Abd El-aziz El-Hashash

eMail

Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, 11566, Cairo, Egypt

Abstract

(E) 2-Cyano-3-phenyl-2-propenoyl chloride reacts with nitrogen, oxygen and sulphur mono- and bi-dentate nucleophilic reagents to give the amide derivatives, the ester derivatives, as well as some heterocyclic systems, namely quinazolinone, pyridopyrimidine and benzothiazepine. Cyclization of some obtained amides affords the benzoxazinones, quinazolinone, whereas that of other amides yields oxadiazole and benzoxazole, respectively.

2_2_200_205_800

This Abstract was viewed 2156 times |

Article PDF downloaded 750 times

How to Cite

(1)

Shiba, S. A.; Madkour, H. M. F.; Hamed, A. A.; Sayed, H. M.; El-Hashash, M. A. E.- aziz. Utility of 2-Cyano-3-Phenyl-2-Propenoyl Chloride As Michael’s Acceptor in Heterocyclic Synthesis With Mono- and Bi-Dentate Nucleophiles. Eur. J. Chem. 2011, 2, 200-205.

Share

Links for Article

Crossref - Scopus - Google - European PMC

Crossref

Scopus

Google Scholar

Europe PMC

References

[1]. Li, Y. L.; Xu, W. F. Bioorgan. Med. Chem. 2004, 12(19), 5171-5180.
doi:10.1016/j.bmc.2004.07.025

[2]. Sousa, J. B.; Calheiros, R.; Rio, V.; Borges, F.; Marques, M. P. M. J. Mol. Struc. 2006, 783(1-3), 122-135.
doi:10.1016/j.molstruc.2005.09.004

[3]. Schwaiger, S.; Cervellati, R.; Seger, C.; Ellmerer, E. P.; About, N.; Renimel, I.; Godenir, C.; André, P.; Gafner, F.; Stuppner, H. Tetrahedron 2005, 61(19), 4621-4630.
doi:10.1016/j.tet.2005.03.002

[4]. Wu, C. C.; Wang, T. W.; Wang, W. Y.; Hsieh, P. W.; Wu, Y. C. Eur. J. Pharm. Sci. 2005, 527(1-3), 37-43.
doi:10.1016/j.ejphar.2005.10.023

[5]. Rieu, J. P.; Duflos, A.; Tristani, J. C.; Patoiseau, J. F.; Tisne-Versailles, J.; Bessac, A. M.; Bonnafous, R.; Marty, A.; Verscheure, Y.; Bigg, D. C. H. Eur. J. Med. Chem. 1993, 28(9), 683-691.
doi:10.1016/0223-5234(93)90027-C

[6]. Blackburn, C.; LaMarche, M. J.; Brown, J.; Che, J. L.; Cullis, C. A.; Lai, S.; Magurie, M.; Marsilje, T.; Geddes, B.; Govek, E.; Kadambi, V.; Doherty, C.; Dayton, B.; Brodjian, S.; Marsh, K. C.; Collins, C. A.; Kym, P. R. Bioorgan. Med. Chem. Lett. 2006, 16(10), 2621-2627.
doi:10.1016/j.bmcl.2006.02.044

[7]. Rida, S. M.; Ashour, F. A.; El-Hawash, S. A. M.; El-Semary, M. M.; Badr, M. H.; Shalaby, M. A. Eur. J. Med. Chem. 2005, 40(9), 949-959.
doi:10.1016/j.ejmech.2005.03.023
PMid:16040162

[8]. Lavergne, O.; Fernandes, A-C.; Bréhu, L.; Sidhu, A.; Brézak, M-C.; Prévost, G.; Ducomnun, B.; Contour-Galceru, M. O. Bioorgan. Med. Chem. Lett. 2006, 16(1), 171-175.
doi:10.1016/j.bmcl.2005.09.030

[9]. Lopez-Tudanca, P. L.; Labeaga, L.; Innerarity, A.; Alonsocires, L.; Tapia, I.; Mosquera, R.; Orjales, A. Bioorgan. Med. Chem. 2003, 11(13), 2709-2714.
doi:10.1016/S0968-0896(03)00243-8

[10]. Palmer, J. T.; Hirschbein, B. L.; Cheung, H.; McCarter, J.; Janc, J. W.; Yu, Z. W.; Wesolowski, G. Bioorgan. Med. Chem. Lett. 2006, 16(11), 2909-2914.
doi:10.1016/j.bmcl.2006.03.001

[11]. Madkour, H. M. F.; Shiba, S. A.; Sayed, H. M.; Hamed, A. A. Sulfur Lett. 2001, 24(4), 151-179.

[12]. Madkour, H. M. F.; Farag, A. A.; Ramses, S. Sh.; Ibrahiem, N. A. A. Phosphorus Sulfur 2006, 181, 255-265.
doi:10.1080/104265090970241

[13]. Nofal, Z. M.; El-Zahar, M. I.; Salem, M. A. I.; Madkour, H. M. F. Egypt. J. Chem. 2005, 48(5), 587-604.

[14]. Nofal, Z. M.; Fahmy, H. H.; Madkour, H. M. F.; Zareaa, E. S.; Hassan, S. A. Egypt. J. Pharm. 2006, 5(1), 45-60.

[15]. Madkour, H. M. F.; Mahmoud, M. R.; Sakr A. M.; Habashy, M. M. Sci. Pharm. 2001, 69, 33-52.

[16]. Madkour, H. M. F.; Salem M. A. I.; Soliman, E. A.; Mahmoud, N. F. H. Phosphorus Sulfur 2001, 170, 15-27.
doi:10.1080/10426500108040582

[17]. Salem, M. A. I.; Madkour, H. M. F.; Soliman, E. A.; Mahmoud, N. F. H. Heterocycles 2000, 53(5), 1129-1143.
doi:10.3987/COM-98-8232

[18]. Shiba, S. A. Phosphorus Sulfur 1996, 114, 29-37.
doi:10.1080/10426509608046408

[19]. Shiba, S. A.; Fahmy, A. F. M.; Abdel-Hamid, H. A.; Massoud, M. S. Egypt. J. Chem. 1993, 36, 409-418.

[20]. Abdel-Hamid, H. A.; Fahmy, A. F.; Shiba, S. A.; El-Hawary, N. A. Egypt. J. Chem. 1993, 36, 167-175.

[21]. Shiba, S. A. Arch. Pharm. 1998, 331, 91-96.
doi:10.1002/(SICI)1521-4184(199803)331:3<91::AID-ARDP91>3.0.CO;2-E

[22]. Jaafar, I.; Francis, G.; Danion-Bougot, R.; Danion, D. Synthesis 1994, 1, 56-60.
doi:10.1055/s-1994-25405

[23]. Wang, T. C.; Chen, Y. L.; Lee, K. H.; Tzeng, C. C. Tetrahedron Lett. 1996, 37(35), 6369-6370.
doi:10.1016/0040-4039(96)01364-0

[24]. March, J. Advanced Organic Chemistry, 3rd edition, John Wiley & Sons. Interscience Pub., New York p 1053, 1985.

Most read articles by the same author(s)

Most read articles by the same author(s)

Hassan Mohamed Fawzy Madkour, Ameen Abd El-Maksode Afify, Abdelaal Alameddin Abdallaha, Galal Abd Elmegeed Elsayed, Marwa Sayed Salem, Synthetic utility of enaminoester moiety in heterocyclic synthesis , European Journal of Chemistry: Vol. 1 No. 4 (2010): December 2010
Marwa Sayed Salem, Magda Ismail Marzouk, Salma Nasser Ali, Hassan Mohamed Fawzy Madkour, Synthesis, structure characterization and biological evaluation of new 6,8-dichloro-2-methyl-4H-chromen-4-one derivatives , European Journal of Chemistry: Vol. 3 No. 2 (2012): June 2012
Mahmoud Refaee Mahmoud, Ahmed Kamel El-Ziaty, Mahmoud Fawzy Ismail, Sayed Ahmed Shiba, Synthesis of novel pyrimidine and fused pyrimidine derivatives , European Journal of Chemistry: Vol. 2 No. 3 (2011): September 2011
Marwa Sayed Salem, Maher Abd El-Aziz Mahmoud El-Hashash, Al-Shimaa Omar Ali Mahmoud, Hassan Mohamed Fawzy Madkour, Facile synthesis of new fused and non-fused heterocyclic systems from a γ-ketoacid , European Journal of Chemistry: Vol. 5 No. 1 (2014): March 2014
Mahmoud Refaee Mahmoud, Hassan Mohamed Fawzy Madkour, Eman Abd El-Fattah El-Bordany, El-Sayed Ahmed Soliman, Synthesis and reactions of (Z)-2-imino-5-(3,4,5-trimethoxy benzylidene)thiazolidin-4(H)one , European Journal of Chemistry: Vol. 2 No. 4 (2011): December 2011

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).