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Synthesis 2016; 48(20): 3537-3543
DOI: 10.1055/s-0035-1561861
DOI: 10.1055/s-0035-1561861
paper
Synthesis of Aminopyrazoles from Isoxazoles: Comparison of Preparative Methods by in situ NMR Analysis
Further Information
Publication History
Received: 03 April 2016
Accepted: 20 April 2016
Publication Date:
24 May 2016 (online)
Abstract
A single-step method and a two-step method for the synthesis of aminopyrazoles from isoxazoles are presented and compared. Based on in situ NMR monitoring, both processes proceed through a ketonitrile. In the single-step process, hydrazine serves to both open the isoxazole to the unisolated ketonitrile intermediate and form the aminopyrazole. The two-step process involves ring opening of the isoxazole by deprotonation with hydroxide to generate the ketonitrile followed by the addition of acetic acid and hydrazine to form the aminopyrazole.
Key words
aminopyrazoles - isoxazoles - in situ NMR analysis - ketonitriles - heterocycles - regioselectivitySupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561861.
- Supporting Information
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