Reactions of α-haloacroleins with azides: highly regioselective synthesis of formyl triazoles

A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H 2 O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2019, Vol.21 (15), p.4211-4216
Main Authors: Zhang, Dongsheng, Fan, Yingzhu, Yan, Zhongliang, Nie, Yi, Xiong, Xingquan, Gao, Lizhu
Format: Article
Language:English
Subjects:
Aldehydes
Aliphatic compounds
Azides (organic)
Crystallography
Green chemistry
Protons
Regioselectivity
Substrates
Triazoles
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Summary:A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H 2 O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol is convenient and scalable with a broad substrate scope including aliphatic and aromatic azides. The resulting triazoles exhibited an aldehyde group at the C4 position and demonstrated synthetic utilizations. One 1,2,3-triazole compound containing diastereotopic protons was also identified.
ISSN:1463-9262
1463-9270
DOI:10.1039/C9GC01129C