CH-Diazomethane Sulfonamides Generated in Situ for Intramolecular [3+2] Cycloaddition of Alkynes: An Entry into Novel Pyrazole-Fused Five-Membered Sultams

Abstract

Previously reported CH-diazomethane sulfonamides carrying various propargylic groups are generated in situ from their acetyl precursors. Without purification, these compounds undergo a slow, albeit clean and efficient, intramolecular [3+2] cycloaddition to give pyrazole-fused five-membered sultams. The latter are the first analogues of medicinally important (hetero)arene-fused five-membered sultams containing a five-membered nitrogenous heterocycle. The newly introduced scaffold can be further elaborated into N-arylated derivatives using the Chan–Evans–Lam protocol. The resulting compounds incorporate more than one privileged moiety and are highly suitable for interrogation of protein targets via biological screening.

Key words

diazo compounds - sultams - pyrazoles - [3+2] intramolecular cycloaddition - Mitsunobu alkylation - Chan–Evans–Lam arylation

Publication History

Received: 18 November 2020

Accepted after revision: 14 December 2020

Accepted Manuscript online:
14 December 2020

Article published online:
25 January 2021

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