An efficient synthesis of 4,5-disubstituted-2H-1,2,3-triazoles from nitroallylic derivatives via a cycloaddition–denitration process

A metal-free convenient synthesis of 4,5-disubstituted N-unsubstituted 1,2,3-triazoles via a cycloaddition–denitration process has 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 s...

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Bibliographic Details
Published in:New journal of chemistry 2018-01, Vol.42 (2), p.980-987
Main Authors: Reddy, Raju Jannapu, Waheed, Md, Thatikonda Karthik, Shankar, Angothu
Format: Article
Language:English
Subjects:
Acetates
Alcohols
Chemical synthesis
Cycloaddition
Denitration
Functional groups
Sulfones
Triazoles
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Summary:A metal-free convenient synthesis of 4,5-disubstituted N-unsubstituted 1,2,3-triazoles via a cycloaddition–denitration process has 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 structurally-modifiable triazolylazides and sulfone derived triazoles, respectively, in moderate to good yields. The present protocol is operationally simple, tolerates a broad range of functional groups and is also reliable in the case of a gram scale reaction under optimised reaction conditions. A practically-straightforward gram scale reaction for the synthesis of triazole directly from β-nitrostyrene via a sequential one-pot Morita–Baylis–Hillman and cycloaddition reactions has been achieved.
ISSN:1144-0546
1369-9261
DOI:10.1039/c7nj03292g