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

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• 作者：Dao-Lin Wang ; ^{wangdaolin@sina.com" class="auth_mail" title="E-mail the corresponding author} ; Xiao-Ce Shi ; Yong-Yang Wang ; Jian Ma
• 关键词：4-Bromomethylquinoline-2-one ; 5-Cyano-6-thioxopyrimidine ; Pyrimido[4&prime ; 5&prime ; 5 ; 4]thieno[2 ; 3-e][1 ; 6]naphthyridine ; Thorpe&ndash ; Ziegler reaction ; Pictet&ndash ; Spengler reaction
• 刊名：Chinese Chemical Letters
• 出版年：2016
• 出版时间：February 2016
• 年：2016
• 卷：27
• 期：2
• 页码：261-264
• 全文大小：360 K

文摘

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.