European Journal of Chemistry

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

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Published: Jun 30, 2016
DOI: https://doi.org/10.5155/eurjchem.7.2.230-237.1432
Keywords:
Naphthopyran, α-Cyanocinnamonitriles, Ethyl α-cyanocinnamates, Naphthopyranopyrimidines, 4-Phenyldiazenyl-1-naphthol, 4-(p-Tolyldiazenyl)-1-naphthol
Section
Research Article
Issue
Vol. 7 No. 2 (2016): June 2016
Dates
Received 2016-03-27
Accepted 2016-04-23
Published 2016-06-30


Main Article Content

Ibrahim Ali Radini
Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
Ashraf Hassan Fekry Abd El-Wahab
Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia

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.


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Radini, I. A.; Abd El-Wahab, A. H. F. Heteroaromatization With 4-Phenyldiazenyl-1-Naphthol. Part I: Synthesis of Some New Naphthopyrans and Naphthopyranopyrimidines. Eur. J. Chem. 2016, 7, 230-237.

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