European Journal of Chemistry 2017, 8(3), 240-247 | doi: https://doi.org/10.5155/eurjchem.8.3.240-247.1599 | Get rights and content

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Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part II: Synthesis of some new benzochromens, benzochromenopyrimidines, benzochromenotriazolopyrimidines, benzochromenopyrimidotriazepine and antimicrobial activities


Ibrahim Ali Radini (1) , Hany Mostafa Hamed (2) , Mohammed Abdo Yahya Kharir (3) , Ashraf Hassan Fekry Abd Elwahab (4,*)

(1) Department of Chemistry, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
(2) Chemistry Department, Faculty of Science, Al-Azhar University, 11884, Nasr City, Cairo, Egypt
(3) Department of Chemistry, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
(4) Department of Chemistry, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
(*) Corresponding Author

Received: 12 Jun 2017 | Revised: 03 Jul 2017 | Accepted: 12 Jul 2017 | Published: 30 Sep 2017 | Issue Date: September 2017

Abstract


Synthesis of several new of benzochromenes (4-7), benzochromenopyrimidines (8 and 9), 14-(4-chlorophenyl)-12-(phenyldiazenyl)-14H-benzo[7,8]chromeno[3,2-e][1, 2, 4]triazolo[1, 5-c]pyrimidines, 4-amino-16-(4-chlorophenyl)-14-(phenyldiazenyl)-16H-benzo[7', 8']chro-meno[2',3':4,5]pyrimido[1,6-b][1,2,4]triazepine-3-carbonitrile (10a-e, 13) and 9-(benz-ylideneamino)-7-(4-chlorophenyl)-5-(phenyldiazenyl)-7, 9-dihydro-8H-benzo[7,8]chromeno [2,3-d]pyrimidin-8-imine (12), form starting from 2-amino-4-(p-chlorophenyl)-6-phenyl-diazenyl-4H-benzochromene-3-carbonitrile (3). The structure of these new compounds was confirmed using IR, 1H NMR and 13C NMR as well as MS spectroscopy. The structure activity relationship studies of the target compounds in agreement with the in vitro essays and confirmed higher potent antimicrobial activity against some of the tested microorganisms. The structure-activity relationship study revealed that the antimicrobial activity of benzochromenopyrimido triazepine nucleus was more beneficial than benzochromeno-triazolopyrimidine nucleus for antimicrobial activity.


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Keywords


Benzochromene; Antimicrobial activities; Benzochromenopyrimidine; 4-Phenenyldiazenyl-1-naphthol; Benzochromenotriazolopyrimidine; Benzochromenopyrimidotriaziepine

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DOI: 10.5155/eurjchem.8.3.240-247.1599

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Funding information


the Regional Center for Mycology & Biotechnology (RCMP), Al-Azhar University, Cairo, Egypt

Citations

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[1]. Zhenhua Li, Dayou Rong, Yingyan Cao, Ronghui Hu, Guoqing Huang
Efficient Synthesis of Novel Spiro[indoline-3,5'-pyrano[2,3-d]pyrimidin]-2-one Derivatives and Antitumor Activity Evaluation
HETEROCYCLES  104(7), , 2022
DOI: 10.3987/COM-22-14658
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How to cite


Radini, I.; Hamed, H.; Kharir, M.; Elwahab, A. Eur. J. Chem. 2017, 8(3), 240-247. doi:10.5155/eurjchem.8.3.240-247.1599
Radini, I.; Hamed, H.; Kharir, M.; Elwahab, A. Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part II: Synthesis of some new benzochromens, benzochromenopyrimidines, benzochromenotriazolopyrimidines, benzochromenopyrimidotriazepine and antimicrobial activities. Eur. J. Chem. 2017, 8(3), 240-247. doi:10.5155/eurjchem.8.3.240-247.1599
Radini, I., Hamed, H., Kharir, M., & Elwahab, A. (2017). Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part II: Synthesis of some new benzochromens, benzochromenopyrimidines, benzochromenotriazolopyrimidines, benzochromenopyrimidotriazepine and antimicrobial activities. European Journal of Chemistry, 8(3), 240-247. doi:10.5155/eurjchem.8.3.240-247.1599
Radini, Ibrahim, Hany Mostafa Hamed, Mohammed Abdo Yahya Kharir, & Ashraf Hassan Fekry Abd Elwahab. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part II: Synthesis of some new benzochromens, benzochromenopyrimidines, benzochromenotriazolopyrimidines, benzochromenopyrimidotriazepine and antimicrobial activities." European Journal of Chemistry [Online], 8.3 (2017): 240-247. Web. 4 Jun. 2023
Radini, Ibrahim, Hamed, Hany, Kharir, Mohammed, AND Elwahab, Ashraf. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part II: Synthesis of some new benzochromens, benzochromenopyrimidines, benzochromenotriazolopyrimidines, benzochromenopyrimidotriazepine and antimicrobial activities" European Journal of Chemistry [Online], Volume 8 Number 3 (30 September 2017)

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