陈光旭, 郭荣昆. 长春胺中间体——1—乙基六氢吲(口朶)喹嗪的合成J. 药学学报, 1983, 18(7): 507-513.
引用本文: 陈光旭, 郭荣昆. 长春胺中间体——1—乙基六氢吲(口朶)喹嗪的合成J. 药学学报, 1983, 18(7): 507-513.
CHEN Guang-xü, GUO Rong-kun. SYNTHESIS OF 1-ETHYL-1,2,3,4,6,7-HEXAHYDROINDOLO-2,3a-QUINOLIZINIUM PERCHLORATE——KEY INTERMEDIATE OF VINCAMINEJ. Acta Pharmaceutica Sinica, 1983, 18(7): 507-513.
Citation: CHEN Guang-xü, GUO Rong-kun. SYNTHESIS OF 1-ETHYL-1,2,3,4,6,7-HEXAHYDROINDOLO-2,3a-QUINOLIZINIUM PERCHLORATE——KEY INTERMEDIATE OF VINCAMINEJ. Acta Pharmaceutica Sinica, 1983, 18(7): 507-513.

长春胺中间体——1—乙基六氢吲(口朶)喹嗪的合成

SYNTHESIS OF 1-ETHYL-1,2,3,4,6,7-HEXAHYDROINDOLO-2,3a-QUINOLIZINIUM PERCHLORATE——KEY INTERMEDIATE OF VINCAMINE

  • 摘要: 本文提出了一条不以色胺为原料合成长春胺的关键中间体——高氯酸Wenkert氏烯胺的新途径。由于1-邻苯二甲酰亚胺基-4,5-辛二酮-4-苯腙(Ⅴ)的吲哚合成这一步收率很高,使这一途径成为合成1-正丙基-3,4-二氢-β-卡波林(Ⅶ)及Wenkert氏烯胺(Ⅹ)的较好方法。本文还利用红外光谱、质谱和核磁共振确定了1-邻羧基苯甲酰胺基-4,5-辛二酮-4-苯腙(Ⅳa)和1-正丙基-3,4-二氢-β-卡波林(Ⅶ)存在互变异构现象.

     

    Abstract: This paper describes a new route for the synthesis of 1-ethyl-1,2,3,4, 6, 7-hexahydroindolo-2, 3a-quinolizinium perchlorate(Ⅹ), from which several vinca alkaloids such as vincamine(Ⅰ) and apovincamine(Ⅱ) can be synthesized. Adopting Fischer indole synthesis with common chemicals, this route by-passed the use of the expensive tryptamine. Tautomerism was observed in 1-o-carboxybenzamido-octane-4,5-dione-4-phenyihydrazone(Ⅳa) and in 1-propyl-3, 4-dihydro-β-carboline(Ⅶ).

     

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