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An Efficient One-pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides
Umeå University, Faculty of Science and Technology, Department of Chemistry. Stockholm Univ, Dept Organ Chem, Arrhenius Lab, Stockholm, Sweden.
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
WILEY-V C H VERLAG GMBH , 2017. Vol. 359, no 11, 1990-1995 p.
Keyword [en]
4, 5-dihydroisoxazole, Amides, Reductive functionalization, Chemoselectivity, Enamines
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-137042DOI: 10.1002/adsc.201700154ISI: 000402839300027OAI: oai:DiVA.org:umu-137042DiVA: diva2:1117040
Available from: 2017-06-28 Created: 2017-06-28 Last updated: 2017-06-28Bibliographically approved

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