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Synthesis of N-Sulfonyl Amidines and Acyl Sulfonyl Ureas from Sulfonyl Azides, Carbon Monoxide, and Amides
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.ORCID iD: 0000-0002-3600-0497
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
2017 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 5, p. 2515-2522Article in journal (Refereed) Published
Abstract [en]

A Pd-catalyzed and ligand-free carbonylation/cycloaddition/decarboxylation cascade synthesis of sulfonyl amidines from sulfonyl azides and substituted amides at low CO pressure is reported. The reaction proceeds via an initial Pd-catalyzed carbonylative generation of sulfonyl isocyanates from sulfonyl azides, followed by a [2 + 2] cycloaddition with amides and subsequent decarboxylation, which liberates the desired sulfonyl amidines, generating N-2 and CO2 as the only reaction byproducts. Using this simple protocol, a diverse range of sulfonyl amidines was obtained in moderate to excellent yields. In addition, the reaction can also be directed through a more conventional amidocarbonylation pathway by employing N-monosubstituted amide nucleophiles to afford acyl sulfonyl ureas in good yields.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2017. Vol. 82, no 5, p. 2515-2522
National Category
Medicinal Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-320261DOI: 10.1021/acs.joc.6b02894ISI: 000395726000020PubMedID: 28150496OAI: oai:DiVA.org:uu-320261DiVA, id: diva2:1089142
Funder
Carl Tryggers foundation , CTS13:333 CTS14:356Available from: 2017-04-18 Created: 2017-04-18 Last updated: 2018-01-13Bibliographically approved

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Chow, Shiao Y.Odell, Luke R.

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