| 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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| 引用本文： | 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]. 中国化学快报, 2016, 27(2): 261-264. DOI: 10.1016/j.cclet.2015.10.008 |
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| 作者姓名： | Dao-Lin Wang Xiao-Ce Shi Yong-Yang Wang Jian Ma |
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| 作者单位： | College of Chemistry and Chemical Engineering, Liaoning Key Laboratory of Synthesis and Application of Functional Compound, Bohai University, Jinzhou 121003, China |
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| 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 BF_3·OEt_2 gives pyrimidothieno[1,6]naphthyridines in good yields.
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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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| 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(2): 261-264. DOI: 10.1016/j.cclet.2015.10.008 |
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| Authors: | Dao-Lin Wang Xiao-Ce Shi Yong-Yang Wang Jian Ma |
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| Affiliation: | College of Chemistry and Chemical Engineering, Liaoning Key Laboratory of Synthesis and Application of Functional Compound, Bohai University, Jinzhou 121003, China |
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| Abstract: | 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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| Keywords: | 4-Bromomethylquinoline-2-one 5-Cyano-6-thioxopyrimidine Pyrimido[4' 5':5 4]thieno[2 3-e][1 6]naphthyridine Thorpe-Ziegler reaction Pictet-Spengler reaction |
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