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Transformation of 5-acylated N-fluoroalkyl-1,2,3-triazoles to trifluoromethylated ring-fused isoquinolines, 1,3-oxazines, and 1,3-oxazin-6-ones via ketenimines.

ABSTRACT: A one-pot multistep methodology leading to trifluoromethylated cyclopenta[c]isoquinolines, indeno[1,2-c]isoquinolines, 6,6-difluoro-1,3-oxazines, or 1,3-oxazin-6-ones, based on the reaction of 5-acylated N-pentafluoroethyl-substituted 1,2,3-triazoles is presented. A thermal ring opening of the starting triazoles, followed by a 1,2-acyl shift formed reactive ketenimines which cyclized after a rearrangement in a substrate-specific manner to provide new trifluoromethylated heterocyclic products.

SUBMITTER: Janecky L

PROVIDER: S-EPMC11348844 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Transformation of 5-acylated N-fluoroalkyl-1,2,3-triazoles to trifluoromethylated ring-fused isoquinolines, 1,3-oxazines, and 1,3-oxazin-6-ones via ketenimines.

Janecký Lukáš L Klepetářová Blanka B Beier Petr P

RSC advances 20240827 37

A one-pot multistep methodology leading to trifluoromethylated cyclopenta[c]isoquinolines, indeno[1,2-c]isoquinolines, 6,6-difluoro-1,3-oxazines, or 1,3-oxazin-6-ones, based on the reaction of 5-acylated N-pentafluoroethyl-substituted 1,2,3-triazoles is presented. A thermal ring opening of the starting triazoles, followed by a 1,2-acyl shift formed reactive ketenimines which cyclized after a rearrangement in a substrate-specific manner to provide new trifluoromethylated hete ...[more]

PMID: 39193300

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