2-N-(2′.2′-디에톡시 에틸)아미노 벤즈아미드 유도체의 고리화 반응

Abstract

2-aminobenzamide의 유도체 인 2-amino-1-N-methyl-benzamide, 2-N-benzyl aminobenzamide, 2-N-phenyl aminobenzamide를 강염기 존재하에 α-bromoacetaldehyde diethylacetal과 반응시켜 다음과 같은 화합물을 합성하였다. 즉, 2-amino-1-N-methyl benzamide로 부터는 2-N-alkyl 화합물과 3-methyl 2.4-quinazoline-dione을 각각 합성하였고 2-N-benzyl amino benzamide로 부터는 분자내 고리화반응 생성물인 1-N-benzyl-2H-1.4-benzodiazepin-5-one을, 2-N-phenyl aminobenzamide로 부터는 2-N 위치에 알킬화 반응이 진행되어 2-N-phenyl-(2´.2´-diethoxy ethyl)-amino benzamide를 합성하였다.;2-amino-1-N-methyl benzamide, 2-N-benzyl amino benzamide, 2-N-phenyl amino benzamide of 2-amino benzamide derivatives were reacted with α-bromo acetaldehyde diethyl acetal in basic condition. N-alkylated products were prepared from 2-amino-1-N-methyl benzamide and 2-N-phenyl amino benzamide, 1-N-benzyl-1, 4-benzodiazepin-5-one was prepared from 2-N-benzyl aminobenzamide via intramolecular cyclization. However, 2-amino-1-N-methyl benzamide with sodium amide did not react to 1, 4-benzodiazepin-5-one derivative but 3-methyl-2, 4quinazoline-dione was obtained.