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Domino C-H Sulfonylation and Pyrazole Annulation for Fully Substituted Pyrazole Synthesis in Water Using Hydrophilic Enaminones

Author:
Guo, Yanhui, Wang, Guodong, Wei, Li, Wan, Jie-Ping
Source:
Journal of organic chemistry 2019 v.84 no.5 pp. 2984-2990
ISSN:
1520-6904
Subject:
chemical bonding, chemical structure, hydrazines, hydrophilicity, iodine, isotope labeling, organic chemistry, pyrazoles, sodium bicarbonate, stable isotopes, sulfonylation
Abstract:
The cascade reactions between NH₂-functionalized enaminones and sulfonyl hydrazines have been developed for the synthesis of fully substituted pyrazoles. By making use of the hydrophilic primary amino group in the enaminones, the reactions proceed well in the medium of pure water in the presence of molecular iodine, TBHP, and NaHCO₃ via cascade C-H sulfonylation and pyrazole annulation. The cleavage of the C–N bond in enaminones is confirmed by the experiment using ¹⁵N-labeled enaminone.
Agid:
6323042