THE SYNTHESIS OF ALPHA-METHYLTRYPTOPHANS AND ALPHA-ALKYLTRYPTAMINES
THE SYNTHESIS OF ALPHA-METHYLTRYPTOPHANS AND ALPHA-ALKYLTRYPTAMINES
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DOI：
10.1021/jo01079a021
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发表时间：
1960-01-01
影响因子：
3.6
通讯作者：
SZMUSZKOVICZ, J
中科院分区：
文献类型：
--
作者：
HEINZELMAN, RV;ANTHONY, WC;SZMUSZKOVICZ, J
本文报道了一系列吲哚核5-位可被取代的-烷基吡喃和色胺的合成。通过将适当的芦竹碱与a-硝基丙酸乙酯缩合，然后还原和皂化来制备芦竹碱。色胺的制备方法有四种：a）上述硝基酯脱羧，然后还原硝基; B）硝基烷烃与芦竹碱或c）与吲哚-3-甲醛烷基化，然后还原; d）色氨酸与适当的链烷酸酐反应，然后Wolff-Kishner还原得到的酰氨基酮。
This paper reports the synthesis of a scries of-alkyltryptophans and tryptamines in which the indole nucleus may be substituted in the 5-position. The tryptophans were prepared by condensation of the appropriate gramine with ethyl a-nitropropionate followed by reduction and saponification. The tryptamines were prepared by four procedures: a) decar-boxylation of the above nitroester followedby reduction of the nitro groups; b) alkylation of a nitroparaffin with a gramine or c) with an indole-3-carboxaldehyde, followed by reduction; d) treatment of tryptophan with an appropriate alkanoic anhydride followed by Wolff-Kishner reduction of the resulting acylaminoketone.