Synthesis of Indazoles by the [3+2] Cycloaddition of Diazo
Compounds with Arynes and Subsequent Acyl Migration
Zhijian Liu
Feng Shi
Pablo D. G. Martinez
Cristiano Raminelli
Richard C. Larock
10.1021/jo702062n.s001
https://acs.figshare.com/articles/dataset/Synthesis_of_Indazoles_by_the_3_2_Cycloaddition_of_Diazo_Compounds_with_Arynes_and_Subsequent_Acyl_Migration/2964688
The [3+2] cycloaddition of a variety of diazo compounds with <i>o</i>-(trimethylsilyl)aryl triflates in the presence
of CsF or TBAF at room temperature provides a very direct, efficient approach to a wide range of
potentially biologically and pharmaceutically interesting substituted indazoles in good to excellent yields
under mild reaction conditions. Simple diazomethane derivatives afford <i>N</i>-unsubstituted indazoles or
1-arylated indazoles, depending upon the stoichiometry of the reagents and the reaction conditions, while
dicarbonyl-containing diazo compounds undergo carbonyl migration to afford 1-acyl or 1-alkoxycarbonyl
indazoles selectively.
2008-01-04 00:00:00
reaction conditions
Simple diazomethane derivatives
compound
indazole
TBAF