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Cascade bicyclizations of o-alkynyl aldehydes with thiazolium salts: a new access toward poly-functionalized indeno[2,1-b]pyrroles.

ABSTRACT: A new cascade bicyclization of o-alkynyl aldehydes with thiazolium salts is described, in which 25 examples of densely functionalized indeno[2,1-b]pyrroles are achieved in a functional-group-compatible manner. Thiazole carbenes generated in situ from thiazolium salts play dual roles as reaction partners and as NHC catalysts. The synthetic utility of these bicyclization reactions results in subsequent C-C bond-forming events to rapidly build up molecular complexity.

SUBMITTER: Zhou P

PROVIDER: S-EPMC4547933 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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Cascade bicyclizations of o-alkynyl aldehydes with thiazolium salts: a new access toward poly-functionalized indeno[2,1-b]pyrroles.

Zhou Peng P Hao Wen-Juan WJ Zhang Jin-Peng JP Jiang Bo B Li Guigen G Tu Shu-Jiang SJ

Chemical communications (Cambridge, England) 20150801 65

A new cascade bicyclization of o-alkynyl aldehydes with thiazolium salts is described, in which 25 examples of densely functionalized indeno[2,1-b]pyrroles are achieved in a functional-group-compatible manner. Thiazole carbenes generated in situ from thiazolium salts play dual roles as reaction partners and as NHC catalysts. The synthetic utility of these bicyclization reactions results in subsequent C-C bond-forming events to rapidly build up molecular complexity. ...[more]

PMID: 26178784

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