Synthesis of novel benzo[b]pyrimido[4',5':5,4]thieno[2,3-e][1,6]naphthyridine-8-ones via Pictet–Spengler cyclization  

作　　者：Dao-Lin Wang Xiao-Ce Shi Yong-Yang Wang Jian Ma 

机构地区：[1]College of Chemistry and Chemical Engineering, Liaoning Key Laboratory of Synthesis and Application of Functional Compound, Bohai University

出　　处：《Chinese Chemical Letters》2016年第2期261-264,共4页中国化学快报（英文版）

摘　　要：An efficient method for the synthesis of novel benzo[b]pyrimido[4′,5′：5,4]thieno[2,3e]-[1,6]naphthyridine-8-one derivatives via Pictet-Spengler cyclization is reported. The reaction of 4-（3-aminopyrimido[4,5-d]thieno-2-yl）quinoline-2-ones, which could be obtained from Thorpe-Ziegler isomerization of 4-bromomethylquinoline-2-ones and 5-cyano-1,6-dihydro-4-methyl-2-phenyl-6-thioxopyrimidine,with aromatic aldehydes in the presence of BF3·OEt2 gives pyrimidothieno[1,6]naphthyridines in good yields.An efficient method for the synthesis of novel benzo[b]pyrimido[4′,5′：5,4]thieno[2,3e]-[1,6]naphthyridine-8-one derivatives via Pictet-Spengler cyclization is reported. The reaction of 4-（3-aminopyrimido[4,5-d]thieno-2-yl）quinoline-2-ones, which could be obtained from Thorpe-Ziegler isomerization of 4-bromomethylquinoline-2-ones and 5-cyano-1,6-dihydro-4-methyl-2-phenyl-6-thioxopyrimidine,with aromatic aldehydes in the presence of BF3·OEt2 gives pyrimidothieno[1,6]naphthyridines in good yields.

关 键 词：4-Bromomethylquinoline-2-one 5-Cyano-6-thioxopyrimidine Pyrimido[4′ 5′：5 4]thieno[2-3e][1 6]naphthyridine Thorpe-Ziegler reaction Pictet-Spengler reaction 

分 类 号：O626[理学—有机化学]