- Facile, diversity-oriented, normal-electron-demand Diels-Alder reactions of 6-amino-2 H-pyran-2-ones with diethyl acetylenedicarboxylate, 1,4-naphthoquinone, and N-phenylmaleimide
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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.
- Khatri, Adil I.,Samant, Shriniwas D.
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p. 343 - 350
(2015/02/19)
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