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

Adil I. Khatri; Shriniwas D. Samant

doi:10.1055/s-0034-1379397

Synthesis, Table of Contents

Synthesis 2015; 47(03): 343-350
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

Adil I. Khatri

Department of Chemistry, Institute of Chemical Technology, N. M. Parekh Road, Matunga, Mumbai 400019, India Fax: +91(22)22692102 Email: samantsd@yahoo.com Email: sd.samant@ictmumbai.edu.in

,

Shriniwas D. Samant*

Department of Chemistry, Institute of Chemical Technology, N. M. Parekh Road, Matunga, Mumbai 400019, India Fax: +91(22)22692102 Email: samantsd@yahoo.com Email: sd.samant@ictmumbai.edu.in

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Abstract

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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.

Key words

6-amino-2H-pyrone - normal-electron-demand Diels–Alder reaction - diversity-oriented synthesis - aminobiphenyls - anthraquinones - polycyclic diimides

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References

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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

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