Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Syntheses of Heterocyclic Compounds Containing Nitrogen Utilizing Dioxopyrrolines
Takehiro SANO
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1984 Volume 42 Issue 4 Pages 340-354

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Abstract

This article deals with the synthetic utility of dioxopyrrolines in the field of heterocyclic chemistry, especially on focusing carbon-carbon bond forming reactions, in which they acted as dienophiles on Diels-Alder reaction and also as enophiles on photocycloaddition reaction yielding hydroindoles and 2- azabicyclo [3. 2. 0] heptanes respectively. The latter compounds, strained cyclobutanes, underwent skeletal rearrangements to form various heterocyclic compounds such as hydroindoles, azatropolones, azanorbornenes, azanonanes, dihydropyridones, and dihydropyridines. This methodology was successfully applied to total synthesis of erythrina alkaloids.

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© The Society of Syhthetic Organic Chemistry, Japan
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