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Synthesis of 3,1-Benzothiazines by Cyclisation of 2-Thioformylamino­diphenylacetylenes
Synlett ( IF 1.7 ) Pub Date : 2003-01-01 , DOI: 10.1055/s-2003-42078
David H. Reid , Manuel A. Fernandes

2-Formylaminodiphenylacetylenes, obtained in excellent yield by Sonogashira coupling of (2-iodoaryl)formamides with phenylacetylene, were thionated with P 4 S 1 0 in boiling THF to give 2-thioformylaminodiphenylacetylenes.These acetylenes were cyclised by DBU at ambient temperature to give (4Z)-4-benzylidene-4H-3,1-benzothiazines and small amounts of 2-phenylindoles. The structures of (4Z)-4-benzylidene-6,8-dichloro-4H-3,1-benzothiazine and 3,5-dichloro-2-thioformylaminodiphenylacetylene were established by single crystal X-ray analysis.

中文翻译:

2-硫甲氨基二苯乙炔环化合成3,1-苯并噻嗪

通过(2-碘芳基)甲酰胺与苯乙炔的 Sonogashira 偶联以优异的收率获得 2-甲氨基二苯乙炔,在沸腾的 THF 中用 P 4 S 1 0 硫代化,得到 2-硫甲氨基二苯乙炔。这些乙炔在环境温度下通过 DBU 环化得到( 4Z)-4-苯亚甲基-4H-3,1-苯并噻嗪和少量2-苯基吲哚。(4Z)-4-benzylidene-6,8-dichloro-4H-3,1-benzothiazine 和 3,5-dichloro-2-thioformylaminodiphenylacetylene 的结构是通过单晶 X 射线分析建立的。
更新日期:2003-01-01
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