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

[31] Pictet-Spengler reaction in the synthesis of condensed benzodiazepines: synthesis of 11-hetaryl derivatives of 11,12-dihydroquinazolino[3,2-c][2,3]benzodiazepin-14(6H)-ones
Tolkunov, Andrey S.
Mazepa, Alexander V.
Palamarchuk, Gennadiy V.
Shishkin, Oleg V.
Sujkov, Sergey Yu.
Bogza, Sergey L.
MONATSHEFTE FUR CHEMIE, 2017, 148 (04): : 695 - 701
[32] CARBOXYL-MEDIATED PICTET-SPENGLER REACTION - IMPROVED SYNTHESIS OF 2,3,5,6,11,11B-HEXAHYDRO-3-OXO-1H-INDOLIZINO[8,7-B]INDOLES FROM TRYPTAMINE-2-CARBOXYLIC ACIDS
NARAYANAN, K
COOK, JM
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19): : 5733 - 5736
[33] Synthesis of novel benzo[b]pyrimido[4',5':5,4]thieno[2,3-e][1,6]naphthyridine-8-ones via Pictet–Spengler cyclization
Dao-Lin Wang
Xiao-Ce Shi
Yong-Yang Wang
Jian Ma
Chinese Chemical Letters, 2016, (02) : 261 - 264
[34] Pictet-Spengler cyclization of 3,3-diphenylalanine (DIP) (III), synthesis of optically pure 1,2,3,4-tetrahydro-4-phenyl-3-isoquinolinecarboxylic acids, novel α-amino acids for peptides of biological interest
Parke-Davis Pharmaceutical Res. Div., Warner-Lambert Company, 2800 Plymouth Road, Ann Arbor, MI 48105, United States
SYNTH. COMMUN., 1 (49-56):
[35] PICTET-SPENGLER CYCLIZATION OF 3,3-DIPHENYLALANINE (DIP) .3. SYNTHESIS OF OPTICALLY PURE 1,2,3,4-TETRAHYDRO-4-PHENYL-3-ISOQUINOLINECARBOXYLIC ACIDS, NOVEL ALPHA-AMINO-ACIDS FOR PEPTIDES OF BIOLOGICAL INTEREST
CHEN, HG
GOEL, OP
SYNTHETIC COMMUNICATIONS, 1995, 25 (01) : 49 - 56
[36] Pictet-Spengler Cyclization of 3,3-Diphenylalanine (DIP). III. Synthesis of Optically Pure 1,2,3,4-Tetrahydro-4-phenyl-3-isoquinolineca rboxylic Acids, Novel a-Amino Acids for Peptides of Biological Interest
Chen, H. G.
Goel, O. P.
Synthetic Communications, 1995, 25 (01)
[37] Synthesis of new methylated thieno[2,3-a] and [3,2-b]carbazoles by reductive cyclization of 6-(2′-nitrophenyl)benzo[b]thiophenes obtained by palladium-catalyzed cross-coupling
Ferreira, ICFR
Queiroz, MJRP
Kirsch, G
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (03) : 749 - 754
[38] Aza-Annulation of 1,2,3,4-Tetrahydro-β-carboline Derived Enaminones and Nitroenamines: Synthesis of Functionalized Indolizino[8,7-b]indoles, Pyrido[1,2-a:3,4-b′]diindoles, Indolo[2,3-a]quinolizidine-4-ones and Other Tetrahydro-β-carboline Fused Heterocycles
Avadhani, Anusha
Iniyavan, Pethaperumal
Acharya, Anand
Gautam, Vibha
Chakrabarti, Sriparna
Ila, Hiriyakkanavar
ACS OMEGA, 2019, 4 (18): : 17910 - 17922

← 1 2 3 4 →