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

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Zhijian Liu, Feng Shi, Pablo D. G. Martinez, Cristiano Raminelli, and Richard C. Larock*

Department of Chemistry, Iowa State University, Ames, Iowa 50011

J. Org. Chem., 2008, 73 (1), pp 219–226

DOI: 10.1021/jo702062n

Publication Date (Web): December 8, 2007

Section:

Heterocyclic Compounds (More than One Hetero Atom)

Abstract

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.

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This article has been cited by 25 ACS Journal articles (5 most recent appear below).

Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes
Yuesi Fang, Chunrui Wu, Richard C. Larock, and Feng Shi
The Journal of Organic Chemistry2011 76 (21), 8840-8851
- Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes
  Yuesi Fang, Chunrui Wu, Richard C. Larock, and Feng Shi
  The Journal of Organic Chemistry2011 76 (21), 8840-8851
  A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Synthesis of Substituted Pyrazoles via Tandem Cross-Coupling/Electrocyclization of Enol Triflates and Diazoacetates
David J. Babinski, Hector R. Aguilar, Raymond Still, and Doug E. Frantz
The Journal of Organic Chemistry2011 76 (15), 5915-5923
- Synthesis of Substituted Pyrazoles via Tandem Cross-Coupling/Electrocyclization of Enol Triflates and Diazoacetates
  David J. Babinski, Hector R. Aguilar, Raymond Still, and Doug E. Frantz
  The Journal of Organic Chemistry2011 76 (15), 5915-5923
  The synthesis of 3,4,5-trisubstituted pyrazoles via a tandem catalytic cross-coupling/electrocyclization of enol triflates and diazoacetates is presented. The initial scope of this methodology is demonstrated on a range of differentially substituted ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Synthesis of 3-Substituted Indazoles from Arynes and N-Tosylhydrazones
Pan Li, Jingjing Zhao, Chunrui Wu, Richard C. Larock, and Feng Shi
Organic Letters2011 13 (13), 3340-3343
- Synthesis of 3-Substituted Indazoles from Arynes and N-Tosylhydrazones
  Pan Li, Jingjing Zhao, Chunrui Wu, Richard C. Larock, and Feng Shi
  Organic Letters2011 13 (13), 3340-3343
  Readily available, stable, and inexpensive N-tosylhydrazones react with arynes under mild reaction conditions to afford 3-substituted indazoles in moderate to good yields. The reaction appears to involve a dipolar cycloaddition of in situ generated diazo ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Silver Triflate Catalyzed Reaction of 2-Alkynylbenzaldoxime with Aryne
Hui Ren, Yong Luo, Shengqing Ye, and Jie Wu
Organic Letters2011 13 (10), 2552-2555
- Silver Triflate Catalyzed Reaction of 2-Alkynylbenzaldoxime with Aryne
  Hui Ren, Yong Luo, Shengqing Ye, and Jie Wu
  Organic Letters2011 13 (10), 2552-2555
  A novel and unexpected reaction of 2-alkynylbenzaldoxime with aryne in the presence of silver triflate (10 mol %) under mild conditions is discovered. This reaction proceeds through 6-endo-cyclization, [3 + 2] cycloaddition, and rearrangement, leading to ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Overturning Indolyne Regioselectivities and Synthesis of Indolactam V
Sarah M. Bronner, Adam E. Goetz, and Neil K. Garg
Journal of the American Chemical Society2011 133 (11), 3832-3835
- Overturning Indolyne Regioselectivities and Synthesis of Indolactam V
  Sarah M. Bronner, Adam E. Goetz, and Neil K. Garg
  Journal of the American Chemical Society2011 133 (11), 3832-3835
  We report the design and synthesis of an indolyne that displays a reversal in regioselectivity, in both nucleophilic addition and cycloaddition reactions, compared to typical 4,5-indolynes. Our approach utilizes simple computations to predict ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links