Functionalization of 1N-Protected Tetrazoles by Deprotonation with the Turbo Grignard Reagent

Konstantinos Grammatoglou and Aigars Jirgensons*

*Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, Latvia, Email: aigarsosi.lv

K. Grammatoglou, A. Jirgensons, J. Org. Chem., 2022, 87, 3810-3816.

DOI: 10.1021/acs.joc.1c02926

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Abstract

1N-PMB-protected tetrazoles undergo C-H deprotonation with the turbo Grignard reagent without retro [2 + 3] cycloaddition as side reaction to provide a metalated intermediate, that can be used for reactions with electrophiles such as aldehydes, ketones, Weinreb amides, and iodine. The PMB-protecting group at the tetrazole can be cleaved using oxidative hydrogenolysis and acidic conditions.

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Deprotection of the 1N-PMB Group in Tetrazole Derivatives

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Key Words

Tetrazoles

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ID: J42-Y2022