Reductive Pictet-Spengler cyclization of nitriles in the presence of tryptamine: Synthesis of indolo[2,3-a]quinolizidine, nazlinine, and elaeocarpidine

被引：20

作者：

Diker, K ^{[1
]}

ElBiach, K ^{[1
]}

deMaindreville, MD ^{[1
]}

Levy, J ^{[1
]}

机构：

[1] UNIV REIMS,FAC PHARM,CNRS,LAB TRANSFORMAT SYNTH SUBST NAT,F-51096 REIMS,FRANCE

来源：

JOURNAL OF NATURAL PRODUCTS | 1997年 / 60卷 / 08期

关键词：

D O I：

10.1021/np970191s

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Preparation of tetrahydro-beta-carbolines through catalytic hydrogenation of nitriles in the presence of tryptamine was applied to simple syntheses of indolo[2,3-a]quinolizidine (3), nazlinine (4), and elaeocarpidine (7).

引用

页码：791 / 793

页数：3

共 38 条

[21] CARBOXYL-MEDIATED PICTET-SPENGLER REACTION - DIRECT SYNTHESIS OF 1,2,3,4-TETRAHYDRO BETA-CARBOLINES FROM TRYPTAMINE-2-CARBOXYLIC ACIDS
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[22] 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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[23] TETRACYCLIC INDOLE-DERIVATIVES FROM THE REACTION OF METHYL 2,4-DIOXO-6,6-DIMETHOXYHEXANOATE WITH TRYPTAMINE - INDOLO[2,3-A]QUINOLIZIDINE VS 3,7A-DIAZACYCLOHEPTA[JK]FLUORENE
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[24] Synthesis of Indolo[2,3-a]pyrrolo[3,4-c]carbazoles via the Oxidative Cyclization of Bisindolylmaleimides with Pd(TFA)2/Cu(OAc)2
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[25] SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .28. NOVEL TYPE REARRANGEMENT OF AN INDOLO[2,3-A]QUINOLIZIDINE INTO INDOLIZINO[8,7-B]INDOLE
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[26] Synthesis of 3-deaza-β-hydroxyhistidine derivatives and their use for the preparation of substituted pyrrolo[2,3-c]pyridine-5-carboxylates via the Pictet-Spengler reaction
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[29] Lactone formation as an aid in the NMR characterization of two 3-(1'-hydroxyethyl)indolo[2,3-a]quinolizidine-1-carboxylates: Intermediates for the stereoselective synthesis of tacamine-type indole alkaloids
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[30] PICTET-SPENGLER REACTION IN THE SYNTHESIS OF CONDENSED BENZODIAZEPINES. 2.* SYNTHESIS OF NEW DERIVATIVES OF 11,12-DIHYDROQUINAZOLINE-[3,2-c][2,3]BENZODIAZEPIN-14(6H)-ONES
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