Synthesis of Tetrazolo5,1-aisoquinolines via a Suzuki-Miyaura Coupling Reaction/3 + 2 Cycloaddition Sequence

An efficient copper-catalyzed method for the synthesis of tetrazolo[5,1-a]isoquinolines has been developed starting from alkenyl-1,2-bis(boronates). The domino reaction underwent a Suzuki-Miyaura cross-coupling reaction and an azidation followed by an in situ [3 + 2] cycloaddition. Regioselective sy...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-06, Vol.89 (12), p.8578
Main Authors: Aziz, Sk Md Tarik, Nagarajan, Shalini, Sridhar, Balasubramanian, Ghosh, Subhash, Berrée, Fabienne
Format: Article
Language:English
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Summary:An efficient copper-catalyzed method for the synthesis of tetrazolo[5,1-a]isoquinolines has been developed starting from alkenyl-1,2-bis(boronates). The domino reaction underwent a Suzuki-Miyaura cross-coupling reaction and an azidation followed by an in situ [3 + 2] cycloaddition. Regioselective synthesis has been demonstrated by inverting the Suzuki-Miyaura cross-coupling reaction and the azidation.An efficient copper-catalyzed method for the synthesis of tetrazolo[5,1-a]isoquinolines has been developed starting from alkenyl-1,2-bis(boronates). The domino reaction underwent a Suzuki-Miyaura cross-coupling reaction and an azidation followed by an in situ [3 + 2] cycloaddition. Regioselective synthesis has been demonstrated by inverting the Suzuki-Miyaura cross-coupling reaction and the azidation.
ISSN:1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00526