An Efficient One–pot Procedure for the Direct Preparation of 4,5‐Dihydroisoxazoles from Amides
- 8 May 2017
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 359 (11) , 1990-1995
Abstract
A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5‐amino substituted 4,5‐dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3‐dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5‐dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. magnified imageKeywords
Funding Information
- Swedish Research Council
This publication has 70 references indexed in Scilit:
- A Concise and Versatile Double‐Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma AlkaloidsAngewandte Chemie International Edition, 2012
- Generation of Nitrile Oxides from Oximes Using t-BuOI and Their CycloadditionOrganic Letters, 2011
- Controlled and Chemoselective Reduction of Secondary AmidesJournal of the American Chemical Society, 2010
- Highly efficient synthesis of aldenamines from carboxamides by iridium-catalyzed silane-reduction/dehydration under mild conditionsChemical Communications, 2009
- Synthesis, optimization and structure–activity relationships of 3,5-disubstituted isoxazolines as new anti-tuberculosis agentsEuropean Journal of Medicinal Chemistry, 2009
- Discovery of novel isoxazolines as anti-tuberculosis agentsBioorganic & Medicinal Chemistry Letters, 2007
- A Convenient Method of Generation of Nitrile Oxides by Iodosylbenzene and Its Reaction.NIPPON KAGAKU KAISHI, 2002
- 5‐Amino‐4,5‐dihydroisoxazoles. Part I. 5‐Amino‐3‐aryl‐4‐methylene‐4,5‐dihydroisoxazoles and 4‐aminomethyl‐3‐arylisoxazoles from 5‐amino‐4‐aminomethyl‐3‐aryl‐4,5‐dihydroisoxazolesJournal of Heterocyclic Chemistry, 1980
- Studies on Heteroaromaticity. XIX. Direct 1,3-Dipolar Cycloaddition of Hydroxamoyl Chlorides with EnaminesBulletin of the Chemical Society of Japan, 1968
- The Reactions of Primary Nitroparaffins with Isocyanates1Journal of the American Chemical Society, 1960