티아졸로 디아제핀-베타인의 고리변환반응

Abstract

lH - 2 - Mercapto - 4, 5, 6, 7 - tetrahydro - 1, 3 - diazepine 과 phenacyl bromide를 반응시켜 3 - Phenyl - 5, 6, 7, 8 - tetrahydrothiazolo[3, 2-a][1, 3]diazepine을 만들고, 여기에 친전자성 시약인 phenyl isothiocyanate를 가하여 3 - Phenyl - 9 - phenyl (thiocarbamoyl) - 5, 6, 7, 8 - tetrahydrothiazolo[3, 2-a] [1, 3]diazepinium betaine을 합성하였다. 합성된 betaine에 ethyl bromoacetate, methyl bromoacetate 와 같은 α-haloester 및 chloroacetone, P-methoxyphenacyl bromide p-chlorophenacyl bromide와 같은 α-haloketone 등의 알킬화 시약을 반응시켜 고리변환 반응에 의한 새로운 biheterocyclic compound들을 합성하고, 그 이성질화에 대해 연구하였다.;3-Phenyl-5, 6, 7, 8-tetrahydrothiazolo [3,2-a][1,3] diazepine was reacted with phenyl isothiocyanate as an electrophile to form 3-phenyl-9-phenyl (thiocarbamoyl)- 5, 6, 7, 8-tetrahydrothiazolo [3, 2-a] [1,3] diazepinium betaine. New biheterocyclic compounds via ring transformation were prepared by the reaction of the above betaine with α-haloester and α-haloketone such as ethyl bromoacetate, chloroacetone, and p-methoxyphenacyl bromide. In each ring transformation reaction, two major products considered to be geometrical isomers were obtained, respectively.