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Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles.

ABSTRACT: Desulfonylative alkylation of N-tosyl-1,2,3-triazoles under metal-free conditions leading to β-triazolylenones is reported here. The present study encompasses the synthesis of triazoles with a new substitution pattern in a single step from cyclic 1,3-dicarbonyl compounds and N-tosyl triazole in moderate to high yields. Our synthesis takes place with complete regioselectivity as confirmed by crystallographic analysis which is rationalized by a suitable mechanistic proposal. This method provides an efficient, versatile and straightforward strategy towards the synthesis of new functionalized 1,2,3-triazoles.

SUBMITTER: Pati S 

PROVIDER: S-EPMC8022205 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of <i>N</i>-tosyl-1,2,3-triazoles.

Pati Soumyaranjan S   Almeida Renata G RG   da Silva Júnior Eufrânio N EN   Namboothiri Irishi N N INN  

Beilstein journal of organic chemistry 20210331

Desulfonylative alkylation of <i>N</i>-tosyl-1,2,3-triazoles under metal-free conditions leading to β-triazolylenones is reported here. The present study encompasses the synthesis of triazoles with a new substitution pattern in a single step from cyclic 1,3-dicarbonyl compounds and <i>N</i>-tosyl triazole in moderate to high yields. Our synthesis takes place with complete regioselectivity as confirmed by crystallographic analysis which is rationalized by a suitable mechanistic proposal. This met  ...[more]

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