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Efficient synthesis of 4,5-disubstituted-2H-1,2,3-triazoles from nitroallylic derivatives via cycloaddition-denitration process

Abstract

A metal-free convenient synthesis of 4,5-disubstituted N-unsubstituted 1,2,3-triazoles via cycloaddition-denitration process have been described. A variety of readily available nitroallylic alcohols were reacted smoothly with sodium azide in the presence of p-toluenesulfonic acid (p-TSOH) to form synthetically viable triazolylacetates in good to high yields. Additionally, the nitroallylic acetates and sulfones were converted into a structurally-modifiable triazolylazides and sulfone derived triazoles, respectively in moderate to good yields. The present protocol is a operationally simple, tolerates a broad range of functional groups and also reliable in a gram scale reaction under optimised reaction condition. A practically-straightforward gram scale reaction for synthesis of triazole directly from β-nitrostyrene via a sequential one-pot Morita-Baylis-Hillman and cycloaddition reactions has been achived.

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Publication details

The article was received on 31 Aug 2017, accepted on 03 Dec 2017 and first published on 04 Dec 2017


Article type: Paper
DOI: 10.1039/C7NJ03292G
Citation: New J. Chem., 2017, Accepted Manuscript
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    Efficient synthesis of 4,5-disubstituted-2H-1,2,3-triazoles from nitroallylic derivatives via cycloaddition-denitration process

    R. Jannapu Reddy, W. Md., K. Thatikonda and S. Angothu , New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ03292G

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