TY - JOUR

T1 - CH-Diazomethane Sulfonamides Generated in Situ for Intramolecular [3+2] Cycloaddition of Alkynes

T2 - An Entry into Novel Pyrazole-Fused Five-Membered Sultams

AU - Bubyrev, Andrey

AU - Kantin, Grigory

AU - Dar'in, Dmitry

AU - Krasavin, Mikhail

PY - 2020/12/14

Y1 - 2020/12/14

N2 - 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.

AB - 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.

KW - diazo compounds

KW - sultams

KW - pyrazoles

KW - [3+2] intramolecular cycloaddition

KW - Mitsunobu alkylation

KW - Chan-Evans-Lam arylation

U2 - 10.1055/a-1336-6857

DO - 10.1055/a-1336-6857

M3 - статья

JO - Synthesis

JF - Synthesis

SN - 0039-7881

ER -