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Synthesis of Fused Bicyclic [1,2,3]-Triazoles from ?-Amino Diazoketones.

ABSTRACT: Triazoles are an important class of N-heterocycles that are well known for their broad biological activities. In this work, we would like to demonstrate a direct synthesis of the rare fused bicyclic [1,2,3]-triazoles, employing ?-N-protected amino diazoketones as useful synthetic platforms. The strategy was based on the deprotection of a trifluoroacetamide group for the intramolecular and in situ generation of an ?-diazo imine intermediate, followed by a 5-endo-dig cyclization to construct the bicyclic unit. In this fashion, the synthesis of a series of fused bicyclic [1,2,3]-triazoles could be carried out in good to excellent yields (63-95%).

SUBMITTER: Santiago JV

PROVIDER: S-EPMC6648081 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Synthesis of Fused Bicyclic [1,2,3]-Triazoles from γ-Amino Diazoketones.

Santiago João Victor JV Burtoloso Antonio C B ACB

ACS omega 20190103 1

Triazoles are an important class of N-heterocycles that are well known for their broad biological activities. In this work, we would like to demonstrate a direct synthesis of the rare fused bicyclic [1,2,3]-triazoles, employing γ-<i>N</i>-protected amino diazoketones as useful synthetic platforms. The strategy was based on the deprotection of a trifluoroacetamide group for the intramolecular and in situ generation of an α-diazo imine intermediate, followed by a 5-<i>endo</i>-dig cyclization to c ...[more]

PMID: 31459321

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