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

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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.

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Keywords


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

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DOI: 10.5155/eurjchem.2.2.200-205.365

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Funding information


Ain Shams University, Cairo, Egypt.

Citations

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[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
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[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
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[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
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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. 17 Jan. 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)

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