有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
複素環合成素材としてのメソイオン化合物
加藤 博小林 知重
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ジャーナル フリー

1990 年 48 巻 7 号 p. 672-680

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This review summarizes the authors' own works on the use of mesoionic compounds for the preparation of several heterocyclic systems. From six- to ten-membered cyclic conjugated heterocycles have been prepared by the dipolar cycloadditions of mesoionic compounds, and subsequent extrusions and ring expansions of the adducts. Mesoionic compounds react with 7-heteranorbornadiene derivatives to give two aromatic heterocycles by fragmentation of the ylide intermediates resulting from cycloaddition-extrusion. Other reactions covered in-clude [4π + 6π] cycloadditions, preparation of o-quinonoid heterocycles, cycloaddition-extrusion reactions with cumulenes, intramolecular cycloaddition-extrusion reactions, and tandem cycloadditions. Several features of mesoionic compounds as dipolar building blocks of heterocycles are briefly discussed.

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