Isoquinolin-1(2H)-ones and 1,6-naphthyridin-5(6H)-ones by an N-acylation-SNAr sequence |
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Authors: | Richard A Bunce Baskar NammalwarKrishna Kumar Gnanasekaran Nicholas R Cain |
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Institution: | Department of Chemistry, Oklahoma State University, Stillwater, OK 74078-3071, USA |
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Abstract: | A new synthesis of 2,3-dialkyl-4-carbomethoxyisoquinolin-1(2H)-ones and 6,7-dialkyl-8-carbomethoxy-1,6-naphthyridin-5(6H)-ones is reported. The process involves treatment of a β-enaminoester with 2-fluoro-5-nitrobenzoyl chloride, 2-fluorobenzoyl chloride or 2-chloronicotinoyl chloride followed by heating in the presence of base. The conversion, which proceeds by an N-acylation-SNAr reaction sequence, affords 50–86% yields when R1 is n-alkyl but ≤30% yields when R1 is α-branched. |
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Keywords: | Isoquinolin-1(2H)-ones 1 6-Naphthyridin-5(6H)-ones N-acylation-SNAr sequence SNAr by an N-acyl-β-enaminoester Heteroannulation |
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