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Synthesis 2015; 47(03): 343-350
DOI: 10.1055/s-0034-1379397
DOI: 10.1055/s-0034-1379397
paper
Facile, Diversity-Oriented, Normal-Electron-Demand Diels–Alder Reactions of 6-Amino-2H-pyran-2-ones with Diethyl Acetylenedicarboxylate, 1,4-Naphthoquinone, and N-Phenylmaleimide
Further Information
Publication History
Received: 11 August 2014
Accepted after revision: 13 October 2014
Publication Date:
13 November 2014 (online)
Abstract
A series of 6-amino-4-methoxyphenyl-2H-pyran-2-ones, having an electron-rich diene system, capable of undergoing normal-electron-demand (NED) Diels–Alder reaction, were synthesized. The Diels–Alder reaction of these pyrones with electron-deficient dienophiles – diethyl acetylene dicarboxylate, 1,4-naphthoquinone, and N-phenylmaleimide – followed three different pathways and gave structurally diverse products, aminobenzenes, aminoanthraquinones, and aminopolycyclic diimides, respectively. The amino group at the 6-position activated substantially the pyrone ring towards NED Diels–Alder reaction and the reaction has a potential to generate great structural diversity.
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