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17.7 Product Class 7: Cyclazines

DOI: 10.1055/sos-SD-017-01619

Tominaga, Y.Science of Synthesis, (2004171025.

General Introduction

In 1958, when Boekelheide first reported the synthesis of pyrrolo[2,1,5-cd]indolizine (1) (Scheme 1), a peripheral conjugated aromatic compound with delocalized 10π-electrons, he coined the term cyclazine as a common name.[‌1‌,‌2‌] Subsequently, the term cyclazine has been used to refer to a fused, planar, conjugate three-ring system in which the rings share a central nitrogen atom. Many types of cyclazines have been synthesized since Boekelheide and co-workers reported the synthesis of [2.2.3]cyclazines.[‌3‌‌10‌] Theoretical elu­cidation has also advanced since 1958, and the properties of cyclazines have been clarified.[‌11‌‌18‌] Cyclazine derivatives, which are a type of heteroannulene, peripheral conjugated heteroaromatic compounds with (4n+2)π- or 4nπ-electrons and a nitrogen atom in the center of the rings, are very interesting from a theoretical and chemical points of view. In this article, methods for the synthesis of typical aromatic cyclazines derivatives 17, as shown in Scheme 1, and their nitrogen analogues, are summarized according to the type of cyclazine.

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