Utility of 2-cyano-3-phenyl-2-propenoyl chloride as Michael’s acceptor in heterocyclic synthesis with mono- and bi-dentate nucleophiles
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Published:
Jun 30, 2011
Keywords:
Mono- and bi-dentate nucleophiles,
2-propenoyl chloride,
Benzoxazinone,
Quinazolinone,
Oxadiazole,
Benzoxazole
Section
Research Article
Dates
Received 2010-12-07
Accepted 2011-04-05
Published 2011-06-30
Accepted 2011-04-05
Published 2011-06-30
Main Article Content
Sayed Ahmed Shiba
Hassan Mohamed Fawzy Madkour
Ashraf Ahmed Hamed
Hatem Mohamed Sayed
Maher Abd El-aziz El-Hashash
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.
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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.
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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.
Supporting Agencies
Ain Shams University, Cairo, Egypt.
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