Transition Metal‐Free sp3 C–H Functionalization of Arylacetic Acids for the Synthesis of 1,3,5‐Triazines

A one‐pot simple, efficient and practically viable protocol for the synthesis of substituted 1,3,5‐triazines has been reported from arylacetic acids and benzamidine hydrochloride. In addition, we demonstrated first transition metal‐free conversion of phenylacetic acid to benzaldehyde which on conden...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2018; no. 18; pp. 2098 - 2102
Main Authors Pardeshi, Sachin D., Sathe, Pratima A., Pawar, Balu V., Vadagaonkar, Kamlesh S., Chaskar, Atul C.
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 15.05.2018
Subjects
Arylacetic acid
Benzaldehyde
C‐H Functionalization
Metal‐free
Nitrogen heterocycles
Phenylacetic acid
Synthesis
Triazenes
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Summary:A one‐pot simple, efficient and practically viable protocol for the synthesis of substituted 1,3,5‐triazines has been reported from arylacetic acids and benzamidine hydrochloride. In addition, we demonstrated first transition metal‐free conversion of phenylacetic acid to benzaldehyde which on condensation with two equivalents of benzamidine hydrochloride offered 2,4,6‐trisubstituted 1,3,5‐triazines. This protocol is environmentally benign and economically viable which makes it feasible for gram scale synthesis. An efficient transition metal‐free protocol for the synthesis of 1,3,5‐trisubstituted triazines has been developed through C–H functionalization of arylacetic acids by using K2CO3 as a base, followed by condensation with substituted benzamidine hydrochloride.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800178