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A Two-Step Procedure for the Overall Transamidation of 8-Aminoquinoline Amides Proceeding via the Intermediate N-Acyl-Boc-Carbamates
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-3153-748X
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 32018 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 83, no 8, p. 4464-4476Article in journal (Refereed) Published
Abstract [en]

Herein a two-step strategy for achieving overall transamidation of 8-aminoquinoline amides has been explored. In this protocol, the 8-aminoquinoline amides were first treated with Boc(2)O and DMAP to form the corresponding N-acyl-Boc-carbamates, which were found to be sufficiently reactive to undergo subsequent aminolysis with different amines in the absence of any additional reagents or catalysts. To demonstrate the utility of this approach, it was applied on a number of 8-aminoquinoline amides from the recent C-H functionalization literature, enabling access to a range of elaborate amide derivatives in good to high yields

Place, publisher, year, edition, pages
2018. Vol. 83, no 8, p. 4464-4476
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-156672DOI: 10.1021/acs.joc.8b00174ISI: 000430898500015PubMedID: 29578345OAI: oai:DiVA.org:su-156672DiVA, id: diva2:1212045
Available from: 2018-06-01 Created: 2018-06-01 Last updated: 2018-06-01Bibliographically approved

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