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dc.contributor.authorMookda Pattarawarapanen_US
dc.contributor.authorDolnapa Yamanoen_US
dc.contributor.authorNitaya Wiriyaen_US
dc.contributor.authorWong Phakhodeeen_US
dc.description.abstract© 2019 American Chemical Society. The unprecedented reaction of tertiary amines with 2(3H)-benzoxazolones has been investigated. In the presence of the Ph 3 P-I 2 reagent system, the reaction of both acyclic and cyclic aliphatic tertiary amines led to the formation of 2-N,N-dialkylaminobenzoxazoles with the selective cleavage of an alkyl group. Especially, N-(2-iodoethyl)piperazinyl derivatives were rapidly produced in good yields when using DABCO as the nitrogen source. Only in the cases when the nucleophilicity of the substrates exceeds that of the amine, competitive self-condensation of benzoxazolones then proceeds preferentially. 31 P{ 1 H}-NMR study suggested the involvement of an aryloxyphosphonium intermediate and/or possibly 2-iodobenzoxazole which activates the C-2 position of benzoxazolones toward nucleophilic aromatic substitution.en_US
dc.titleMetal-Free Synthesis of 2-N,N-Dialkylaminobenzoxazoles Using Tertiary Amines as the Nitrogen Sourceen_US
article.title.sourcetitleJournal of Organic Chemistryen_US
article.volume84en_US Mai Universityen_US
Appears in Collections:CMUL: Journal Articles

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