Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
Utility of 2-cyano-3-phenyl-2-propenoyl chloride as Michael’s acceptor in heterocyclic synthesis with mono- and bi-dentate nucleophiles
Sayed Ahmed Shiba (1)
, Hassan Mohamed Fawzy Madkour (2,*) , Ashraf Ahmed Hamed (3) , Hatem Mohamed Sayed (4) , Maher Abd El-aziz El-Hashash (5) (1) Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, 11566, Cairo, Egypt
(2) Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, 11566, Cairo, Egypt
(3) Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, 11566, Cairo, Egypt
(4) Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, 11566, Cairo, Egypt
(5) Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, 11566, Cairo, Egypt
(*) Corresponding Author
Received: 07 Dec 2010 | Revised: 06 May 2011 | Accepted: 05 Apr 2011 | Published: 30 Jun 2011 | Issue Date: June 2011
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.
Keywords
Mono- and bi-dentate nucleophiles; 2-propenoyl chloride; Benzoxazinone; Quinazolinone; Oxadiazole; Benzoxazole
Full Text:
PDF
DOI: 10.5155/eurjchem.2.2.200-205.365
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics
This Abstract was viewed 1558 times |
PDF Article downloaded 512 times
Funding information
Ain Shams University, Cairo, Egypt.
Citations
[1]. Eman A. E. El-Helw, Marwa M. Gado, Ahmed K. El-Ziaty
Synthesis and anti-rotavirus activity of some nitrogen heterocycles integrated with pyrazole scaffold
Journal of the Iranian Chemical Society 17(6), 1479, 2020
DOI: 10.1007/s13738-020-01873-7
[2]. Hanan A. Sallam, Amna S. Elgubbi, Eman A. E. El-Helw
Synthesis and antioxidant screening of new 2-cyano-3-(1,3-diphenyl-1H-pyrazol-4-yl)acryloyl amide derivatives and some pyrazole-based heterocycles
Synthetic Communications 50(13), 2066, 2020
DOI: 10.1080/00397911.2020.1765258
[3]. Roshna V. Nair, Gangadhar J. Sanjayan
(Thio)urea-mediated benzoxazinone opening: mild approach towards synthesis of o-(substituted amido)benzamides
RSC Advances 4(14), 7058, 2014
DOI: 10.1039/c3ra45903a
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.
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.
How to cite
Shiba, S.; Madkour, H.; Hamed, A.; Sayed, H.; El-Hashash, M.
Eur. J. Chem.
2011,
2(2), 200-205.
doi:10.5155/eurjchem.2.2.200-205.365
Shiba, S.; Madkour, H.; Hamed, A.; Sayed, H.; El-Hashash, M. 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(2), 200-205.
doi:10.5155/eurjchem.2.2.200-205.365
Shiba, S., Madkour, H., Hamed, A., Sayed, H., & El-Hashash, M.
(2011).
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, 2(2), 200-205.
doi:10.5155/eurjchem.2.2.200-205.365
Shiba, Sayed, Hassan Mohamed Fawzy Madkour, Ashraf Ahmed Hamed, Hatem Mohamed Sayed, & Maher Abd El-aziz El-Hashash.
"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 [Online], 2.2 (2011): 200-205. Web. 18 May. 2022
Shiba, Sayed, Madkour, Hassan, Hamed, Ashraf, Sayed, Hatem, AND El-Hashash, Maher.
"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 [Online], Volume 2 Number 2 (30 June 2011)
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.2.2.200-205.365
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
European Journal of Chemistry 2011, 2(2), 200-205 | doi: https://doi.org/10.5155/eurjchem.2.2.200-205.365 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2022 • 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 2010-2022 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.