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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 | Revised: 27 Apr 2016 | Accepted: 29 Apr 2016 | Published: 30 Jun 2016 | Issue Date: June 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.
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DOI: 10.5155/eurjchem.7.2.230-237.1432
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Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
Citations
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European Journal of Chemistry 8(4), 358, 2017
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DOI Link: https://doi.org/10.5155/eurjchem.7.2.230-237.1432
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European Journal of Chemistry 2016, 7(2), 230-237 | doi: https://doi.org/10.5155/eurjchem.7.2.230-237.1432 | Get rights and content
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