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Chemistry of aza- and diazafulvenium methides in heterocyclic synthesis
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Chemistry of aza- and diazafulvenium methides in heterocyclic synthesis
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Journal Article
Chemistry of aza- and diazafulvenium methides in heterocyclic synthesis
2016
Overview
Aza- and diazafulvenium methide systems are versatile building blocks for the synthesis of pyrroles and pyrazoles. These extended dipoles participate in sigmatropic [1,8]H shifts and 1,7-electrocyclizations giving vinyl pyrroles and pyrazoles. Under flash vacuum pyrolysis conditions these heterocycles undergo interesting rearrangements. Aza- and diazafulvenium methides can be intercepted by dipolarophiles. Derivatives with carboxylate groups at C-4 and/or C-5 act exclusively as 1,7-dipoles affording products resulting from the addition across the 1,7-positions. These 1,7-cycloadducts include chlorin and bacteriochlorin type macrocycles as well as steroidal analogues, compounds with relevance in medicinal chemistry. In contrast with this chemical behavior, 5-trifluoromethylazafulvenium methides can participate in both 1,7- and 1,3-dipolar cycloadditions. The generation and reactivity of benzodiazafulvenium methides is also discussed.
Publisher
De Gruyter,Walter de Gruyter GmbH
Subject
