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Issue 14, 2014
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α-Haloacrylates as acceptors in the [3 + 2] cycloaddition reaction with NaN3: an expedient approach to N-unsubstituted 1,2,3-triazole-4-carboxylates

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Abstract

An expedient synthesis of N-unsubstituted 1,2,3-triazole-4-carboxylates has been demonstrated through [3 + 2] cycloaddition of sodium azide with α-haloacrylates. The process is highly reliable and exhibits an unusually wide scope with respect to α-fluoro-, α-chloro-, α-bromo-, and α-iodoacrylates. The potential of selected 1,2,3-triazole-4-carboxylates in the preparation of 1,5-dihydro-4H-[1,2,3]-triazolo-[4,5-c]-quinolin-4-one has also been illustrated.

Graphical abstract: α-Haloacrylates as acceptors in the [3 + 2] cycloaddition reaction with NaN3: an expedient approach to N-unsubstituted 1,2,3-triazole-4-carboxylates

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Publication details

The article was received on 14 Nov 2013, accepted on 04 Feb 2014 and first published on 04 Feb 2014


Article type: Paper
DOI: 10.1039/C3OB42276C
Citation: Org. Biomol. Chem., 2014,12, 2280-2288
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    α-Haloacrylates as acceptors in the [3 + 2] cycloaddition reaction with NaN3: an expedient approach to N-unsubstituted 1,2,3-triazole-4-carboxylates

    J. K. Augustine, C. Boodappa and S. Venkatachaliah, Org. Biomol. Chem., 2014, 12, 2280
    DOI: 10.1039/C3OB42276C

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