Prev. Article Next Article Table of Contents

Note

Metal Triflate Catalyzed Reactions of Alkenes, NBS, Nitriles, and TMSN₃: Synthesis of 1,5-Disubstituted Tetrazoles

Supporting Info

Saumen Hajra,* Debarshi Sinha, and Manishabrata Bhowmick

Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India shajra@chem.iitkgp.ernet.in

J. Org. Chem., 2007, 72 (5), pp 1852–1855

DOI: 10.1021/jo062432j

Publication Date (Web): February 1, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

A versatile and highly efficient protocol for the synthesis of 1,5-disubstituted tetrazoles has been developed by metal triflate catalyzed one-pot reaction of alkenes, NBS, nitriles, and TMSN₃. Among the metal triflates, Zn(OTf)₂ was found to be the best catalyst. Use of different combinations of alkenes and nitriles generate a variety of 1,5-disubstituted tetrazoles containing an additional α-bromo functionality of the N1-alkyl substituent.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue March 02, 2007
Received November 27, 2006

Recommend & Share

Related Content

Highly Regio- and Stereoselective Asymmetric Bromoazidation of Chiral α,β-Unsaturated Carboxylic Acid Derivatives: Scope and LimitationsThe Journal of Organic Chemistry
- Highly Regio- and Stereoselective Asymmetric Bromoazidation of Chiral α,β-Unsaturated Carboxylic Acid Derivatives: Scope and Limitations
  Saumen Hajra, Manishabrata Bhowmick, and Debarshi Sinha
  The Journal of Organic Chemistry 2006 71 (24), pp 9237–9240
  Abstract: Lewis acid catalyzed asymmetric bromoazidation of chiral α,β-unsaturated carboxylic acid derivatives was performed using N-bromosuccinimide (NBS) and trimethylsilyl azide (TMSN₃) as the bromine and azide sources. Among the Lewis acids, Yb(OTf)₃ was found ...
  Abstract | Full Text HTML | Hi-Res PDF
Stereoselective One-Pot Synthesis of OxazolinesThe Journal of Organic Chemistry
- Stereoselective One-Pot Synthesis of Oxazolines
  Saumen Hajra, Sukanta Bar, Debarshi Sinha and Biswajit Maji
  The Journal of Organic Chemistry 2008 73 (11), pp 4320–4322
  Abstract: Treatment of alkenes with NBS, a nitrile, NaHCO₃ and water in the presence of Cu(OTf)₂ or Zn(OTf)₂ is reported to furnish oxazolines in one pot and good yields. The reaction is equally applicable to chalcones.
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Stereoselective Construction of Seven-Membered Rings with an All-Carbon Quaternary Center by Direct Tiffeneau−Demjanov-type Ring ExpansionJournal of the American Chemical Society
- Stereoselective Construction of Seven-Membered Rings with an All-Carbon Quaternary Center by Direct Tiffeneau−Demjanov-type Ring Expansion
  Takuya Hashimoto, Yuki Naganawa and Keiji Maruoka
  Journal of the American Chemical Society 2009 131 (18), pp 6614–6617
  Abstract: Insertion of one methylene unit into the C−C bond of cyclohexanones is a potentially useful, straightforward method for the construction of seven-membered carbocycles. An especially appealing but largely unexplored method in this arena is the nucleophilic ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Note

Metal Triflate Catalyzed Reactions of Alkenes, NBS, Nitriles, and TMSN₃: Synthesis of 1,5-Disubstituted Tetrazoles