title: Diacetoxyiodobenzene assisted C-O bond formation via sequential acylation and deacylation process: synthesis of benzoxazole amides and their mechanistic study by DFT.
abstract: An efficient method for the transformation of N-substituted-N'-benzoylthioureas to substituted N-benzoxazol-2-yl-amides using diacetoxyiodobenzene (DIB) is described in this work. The transformation follows the C-O bond formation leading to the benzoxazole derivative, due to oxidative dehydrogenation by DIB, instead of the expected C-S bond formation of the benzothiazole moiety. The C-O bond formation leading to benzoxazole is due to consecutive acylation and deacylation in conjunction with the reduction of two moles of DIB. A plausible mechanism was proposed for the reaction and density functional calculations were also performed to study the reaction mechanism.
authors.affiliation: Department of Chemistry, Manipur University, Canchipur, Imphal 795003, Manipur, India. warjeet@manipuruniv.ac.in warjeet@yahoo.com.
authors.forename: Lokendrajit
authors.initials: L
authors.lastname: Nahakpam
authors.affiliation: Department of Chemistry, Manipur University, Canchipur, Imphal 795003, Manipur, India. warjeet@manipuruniv.ac.in warjeet@yahoo.com.
authors.forename: Francis A S
authors.initials: FA
authors.lastname: Chipem
authors.affiliation: Institute of Bioresources and Sustainable Development, Takyelpat, 795001, Imphal, Manipur, India.
authors.forename: Brajakishor S
authors.initials: BS
authors.lastname: Chingakham
authors.affiliation: Department of Chemistry, Manipur University, Canchipur, Imphal 795003, Manipur, India. warjeet@manipuruniv.ac.in warjeet@yahoo.com.
authors.forename: Warjeet S
authors.initials: WS
authors.lastname: Laitonjam