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Palladium(0)-Catalyzed Carbonylative One-Pot Synthesis of N-Acylguanidines
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry.ORCID iD: 0000-0001-6258-0635
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry.ORCID iD: 0000-0001-7658-5103
2017 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 23, p. 12520-12529Article in journal (Refereed) Published
Abstract [en]

A convenient synthetic strategy toward N-acylguanidines via a sequential one-pot multicomponent carbonylation/amination reaction has been developed. The compounds were readily obtained via an N-cyanobenzamide intermediate formed from the Pd(0)-catalyzed carbonylative coupling of cyanamide and aryl iodides or bromides. Subsequent amination with a large variety of amines provided the final N-acylguanidines, with the overall formation of one C-C and two C-N bonds, in moderate to excellent yields. The substrate scope was found to be wide and the methodology was used to produce over 50 compounds, including 29 novel molecules. Furthermore, three separate nitrogen-containing heterocycles were prepared from the N-acylguanidines synthesized using the developed multicomponent, carbonylative method.

Place, publisher, year, edition, pages
2017. Vol. 82, no 23, p. 12520-12529
National Category
Organic Chemistry
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URN: urn:nbn:se:uu:diva-343509DOI: 10.1021/acs.joc.7b02294ISI: 000417342300056PubMedID: 29027801OAI: oai:DiVA.org:uu-343509DiVA, id: diva2:1186249
Available from: 2018-02-27 Created: 2018-02-27 Last updated: 2018-03-08Bibliographically approved

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Åkerbladh, LindaSchembri, Luke SLarhed, MatsOdell, Luke R.

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