European Journal of Chemistry 2016, 7(2), 230-237. doi:10.5155/eurjchem.7.2.230-237.1432

Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part I: Synthesis of some new naphthopyrans and naphthopyranopyrimidines


Ibrahim Ali Radini (1) , Ashraf Hassan Fekry Abd El-Wahab (2,*)

(1) Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
(2) Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
(*) Corresponding Author

Received: 27 Mar 2016, Accepted: 29 Apr 2016, Published: 30 Jun 2016

Abstract


Reaction of 4-phenyldiazenyl /or 4-(p-tolyldiazenyl)-1-naphthol (1) with various substituted α-cyanocinnamonitriles (2a-h) and ethyl α-cyanocinnamates (2i-p) afforded 2-amino-4-(aryl)-6-(phenyldiazenyl /or p-tolyldiazenyl)-4H-naphtho[1,2-b]pyrano-3-carbonitrile (3a-h) and ethyl 2-amino-4-(aryl)-6-(phenyldiazenyl /or p-tolyldiazenyl)-4H-naphtho[1,2-b]pyrano-3-carboxylate (3i-p). Reaction of compound 3a with Ac2O or PhCOCl and formic acid afforded N-acetylamino or N,N-dibenzoylamino and naphthopyranopyrimidine derivatives (4-8), respectively. The structures of these compounds were established on the basis of IR, UV, 1H NMR, 13C NMR, and MS data.


Keywords


Naphthopyran; α-Cyanocinnamonitriles; Ethyl α-cyanocinnamates; Naphthopyranopyrimidines; 4-Phenyldiazenyl-1-naphthol; 4-(p-Tolyldiazenyl)-1-naphthol

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DOI: 10.5155/eurjchem.7.2.230-237.1432

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How to cite


Radini, I.; Abd El-Wahab, A. Eur. J. Chem. 2016, 7(2), 230-237. doi:10.5155/eurjchem.7.2.230-237.1432
Radini, I.; Abd El-Wahab, A. Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part I: Synthesis of some new naphthopyrans and naphthopyranopyrimidines. Eur. J. Chem. 2016, 7(2), 230-237. doi:10.5155/eurjchem.7.2.230-237.1432
Radini, I., & Abd El-Wahab, A. (2016). Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part I: Synthesis of some new naphthopyrans and naphthopyranopyrimidines. European Journal of Chemistry, 7(2), 230-237. doi:10.5155/eurjchem.7.2.230-237.1432
Radini, Ibrahim, & Ashraf Hassan Fekry Abd El-Wahab. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part I: Synthesis of some new naphthopyrans and naphthopyranopyrimidines." European Journal of Chemistry [Online], 7.2 (2016): 230-237. Web. 16 Sep. 2019
Radini, Ibrahim, AND Abd El-Wahab, Ashraf. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part I: Synthesis of some new naphthopyrans and naphthopyranopyrimidines" European Journal of Chemistry [Online], Volume 7 Number 2 (30 June 2016)

DOI Link: https://doi.org/10.5155/eurjchem.7.2.230-237.1432

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