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

Desulfonylative alkylation of -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 -tosyl triazole in modera...

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Published inBeilstein journal of organic chemistry Vol. 17; no. 1; pp. 762 - 770
Main Authors Pati, Soumyaranjan, Almeida, Renata G, da Silva Júnior, Eufrânio N, Namboothiri, Irishi N N
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 31.03.2021
Beilstein-Institut
Subjects
1,2,3-triazoles
Alkylation
azoles
Chemistry
Chromatography
cycloaddition
enones
heterocycles
Letter
Triazoles
cycloaddition
azoles
heterocycles
enones
1,2,3-triazoles
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Summary:Desulfonylative alkylation of -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 -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.
Bibliography:ObjectType-Article-1
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ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.17.66