Effect of Sulfamic Acid on 1,3-Dipolar Cycloaddition Reaction: Mechanistic Studies and Synthesis of 4-Aryl-NH-1,2,3-triazoles from Nitroolefins | Health & Environmental Research Online (HERO)

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Citation
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HERO ID

4274497

Reference Type

Journal Article

Title

Effect of Sulfamic Acid on 1,3-Dipolar Cycloaddition Reaction: Mechanistic Studies and Synthesis of 4-Aryl-NH-1,2,3-triazoles from Nitroolefins

Author(s)

Sharma, P; Kumar, NP; Senwar, KR; Forero-Doria, O; Nachtigall, FM; Santos, LS; Shankaraiah, N

Year

2017

Is Peer Reviewed?

Yes

Journal

Journal of the Brazilian Chemical Society
ISSN: 0103-5053
EISSN: 1678-4790

Volume

Issue

Page Numbers

589-597

Language

English

DOI

10.21577/0103-5053.20160203

Web of Science Id

WOS:000396347700009

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-85014430554&doi=10.21577%2f0103-5053.20160203&partnerID=40&md5=1825de6f3d47cc52febf4ba7ba3f54d9
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Abstract

A facile and new metal-free 1,3-dipolar cycloaddition reaction for the synthesis of 4-aryl-NH-1,2,3-triazoles from nitroolefins and NaN3 employing NH2SO3H has been developed. Sulfamic acid proved to be an efficient additive in this transformation by inhibiting the formation of triaryl benzene. Mechanistic aspects and key intermediates associated with this transformation have also been characterized by online monitoring of the reaction using electrospray ionization tandem mass spectrometry method (ESI-MS/MS). The protocol emphasizes broad substrate scope for many functionalities, simple reaction conditions such as stability to open air, less reaction time, easy work-up, eco-friendly and with good to excellent yields.

Keywords

bioactive triazoles; electrospray ionization; reaction mechanism; green chemistry