Synthesis of Indazoles by the [3+2] Cycloaddition of Diazo Compounds with Arynes and Subsequent Acyl Migration

The [3+2] cycloaddition of a variety of diazo compounds with o-(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 ex...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-01, Vol.73 (1), p.219-226
Main Authors: Liu, Zhijian, Shi, Feng, Martinez, Pablo D. G, Raminelli, Cristiano, Larock, Richard C
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Azo Compounds - chemistry
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Indazoles - chemical synthesis
Indazoles - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:The [3+2] cycloaddition of a variety of diazo compounds with o-(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 N-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo702062n