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An Efficient One-pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry. Umeå University, Sweden.
Number of Authors: 4
2017 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 359, no 11, 1990-1995 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2017. Vol. 359, no 11, 1990-1995 p.
Keyword [en]
4, 5-dihydroisoxazole, Amides, Reductive functionalization, Chemoselectivity, Enamines
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-144789DOI: 10.1002/adsc.201700154ISI: 000402839300027OAI: oai:DiVA.org:su-144789DiVA: diva2:1127310
Available from: 2017-07-14 Created: 2017-07-14 Last updated: 2017-09-08Bibliographically approved
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