100817-78-5Relevant articles and documents
Diacetoxyiodobenzene assisted C-O bond formation: Via sequential acylation and deacylation process: Synthesis of benzoxazole amides and their mechanistic study by DFT
Nahakpam, Lokendrajit,Chipem, Francis A. S.,Chingakham, Brajakishor S.,Laitonjam, Warjeet S.
supporting information, p. 7735 - 7745 (2016/08/24)
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.
