Expanding available pyrazole substitution patterns by sydnone cycloaddition reactions

Abstract

We report the use of alkynylsilanes for the regiocontrolled synthesis of pyrazoles from functionalised sydnones. The strategies outlined herein allow a range of pyrazoles to be accessed with substitution patterns that are otherwise not directly obtained with high selectivity by alkyne cycloadditions. Moreover, this study serendipitously highlighted a simple and convenient procedure for the synthesis of aryl monofluoromethyl ethers through the combination of TBAF and dichloromethane.

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Authors/Creators:	Brown, A.W. Harrity, J.P.A.
Copyright, Publisher and Additional Information:	© 2017 Elsevier. This is an author produced version of a paper subsequently published in Tetrahedron. Uploaded in accordance with the publisher's self-archiving policy. Article available under the terms of the CC-BY-NC-ND licence (https://creativecommons.org/licenses/by-nc-nd/4.0/).
Keywords:	Sydnones; Pyrazoles; Regioselective; Cycloaddition
Dates:	Accepted: 20 April 2017 Published (online): 22 April 2017 Published: 1 June 2017
Institution:	The University of Sheffield
Academic Units:	The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield)
Depositing User:	Symplectic Sheffield
Date Deposited:	30 May 2017 10:40
Last Modified:	22 Apr 2019 00:43
Published Version:	https://doi.org/10.1016/j.tet.2017.04.049
Status:	Published
Publisher:	Elsevier
Refereed:	Yes
Identification Number:	https://doi.org/10.1016/j.tet.2017.04.049

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Expanding available pyrazole substitution patterns by sydnone cycloaddition reactions

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