Citation: Dao-Lin Wang, Xiao-Ce Shi, Yong-Yang Wang, Jian Ma. Synthesis of novel benzo[b]pyrimido[4',5':5,4]thieno[2,3-e][1,6]naphthyridine-8-ones via Pictet-Spengler cyclization[J]. Chinese Chemical Letters, ;2016, 27(02): 261-264. doi: 10.1016/j.cclet.2015.10.008 shu

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

1.
College of Chemistry and Chemical Engineering, Liaoning Key Laboratory of Synthesis and Application of Functional Compound, Bohai University, Jinzhou 121003, China

Corresponding author: Dao-Lin Wang,
Received Date: 17 August 2015
Available Online: 20 September 2015

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.
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