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A short synthesis of quinazolinocarboline alkaloids rutaecarpine, hortiacine, euxylophoricine A and euxylophoricine D from methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)anthranilates
Tetrahedron Letters ( IF 1.5 ) Pub Date : 27 May 2002 , DOI: 10.1016/s0040-4039(02)00711-6 Pramod K. Mohanta , Kyongtae Kim
Tetrahedron Letters ( IF 1.5 ) Pub Date : 27 May 2002 , DOI: 10.1016/s0040-4039(02)00711-6 Pramod K. Mohanta , Kyongtae Kim
Reactions of methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)anthranilates with tryptamine at room temperature produced 2-cyano-3-[2-(indol-3-yl)ethyl]-4(3H)-quinazolinones, which underwent cyclization on heating with TFAA/HCl(g) to afford quinazolinocarboline alkaloids rutaecarpine (1a), hortiacine (1b), euxylophoricine A (1c) and euxylophoricine D (1d) in excellent yields.
中文翻译:
由N-(4-氯-5 H -1,2,3-二噻唑-5-亚萘基)邻氨基苯甲酸甲酯短合成喹唑啉基咔啉生物碱rutaecarpine,hortiacine,euxylophoricine A和euxylophoricine D
甲基的反应ñ - (4-氯-5- ħ -1,2,3- dithiazol -5-亚基)与邻氨基苯甲酸的色胺在室温下,得到2-氰基-3- [2-(吲哚-3-基)乙基] -4(3 H)-喹唑啉酮,与TFAA / HCl(g)加热后进行环化反应,以极好的收率得到喹唑啉羰基碱类生物碱芸香芸香碱(1a),何丁香碱(1b),正丁香碱A(1c)和正丁香碱D(1d)。
更新日期:2017-01-31
中文翻译:
由N-(4-氯-5 H -1,2,3-二噻唑-5-亚萘基)邻氨基苯甲酸甲酯短合成喹唑啉基咔啉生物碱rutaecarpine,hortiacine,euxylophoricine A和euxylophoricine D
甲基的反应ñ - (4-氯-5- ħ -1,2,3- dithiazol -5-亚基)与邻氨基苯甲酸的色胺在室温下,得到2-氰基-3- [2-(吲哚-3-基)乙基] -4(3 H)-喹唑啉酮,与TFAA / HCl(g)加热后进行环化反应,以极好的收率得到喹唑啉羰基碱类生物碱芸香芸香碱(1a),何丁香碱(1b),正丁香碱A(1c)和正丁香碱D(1d)。