Novel synthesis of 2H-1,5-benzoxathiepin-3(4H)-one and 5H-4,1-benzoxathiepin-3(2H)-one derivatives and chemical properties evaluation

Abstract

New methods for the synthesis of 2H-1,5-benzoxathiepin-3(4H)-one and 5H-4,1-benzoxathiepin-3(2H)-one derivatives have been developed. Carbonyl group of 2H-1,5-benzoxathiepin-3(4H)-one has been protected by cyclic and acyclic ketals. Interaction of 2H-1,5-benzoxathiepin-3(4H)-one with NaBH 4 , hydroxylamine, hydrazines, and Br 2 has been investigated. Strecker reaction has been carried out for the synthesis of corresponding a-amino acid. Combination of Horner-WadsworthEmmons and Michael reactions allowed to obtain derivatives of b-substituted carboxylic acid. Also, 2H-1,5-benzoxathiepin-3(4H)-one have been involved in JohnsonCorey-Chaykovsky reaction. Graphical abstract