Intramolecular Heck reaction of 2- and 3-iodoindole derivatives for the synthesis of β- and γ-carbolinones

被引：48

作者：

Beccalli, EM

Broggini, G

Marchesini, A

Rossi, E

机构：

[1] Univ Milan, Fac Farm, Ist Chim Organ, I-20133 Milan, Italy

[2] Univ Insubria, Dipartimento Sci Chim Fis & Matemat, I-22100 Como, Italy

来源：

TETRAHEDRON | 2002年 / 58卷 / 33期

关键词：

Heck reaction; Pd catalyst; intramolecular cyclization; indoles; carbolines;

D O I：

10.1016/S0040-4020(02)00688-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of beta- and gamma-carbolinone derivatives was achieved by an intramolecular Heck cyclisation from the corresponding 3-iodo-1H-indole-2-carboxylic acid allyl-amides 8 and 2-iodo-1H-indole-3-carboxylic acid allyl-amides 9. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：6673 / 6678

页数：6

共 27 条

[1] Abbiati G, 2001, SYNTHESIS-STUTTGART, P2477
[2] An alternative approach to the synthesis of functionalized pyrido[2,3-b]indoles
Beccalli, EM
Clerici, F
Marchesini, A
[J]. TETRAHEDRON, 2001, 57 (22) : 4787 - 4792
[3] 2-(QUINUCLIDIN-3-YL)PYRIDO[4,3-B]INDOL-1-ONES AND ISOQUINOLIN-1-ONES - POTENT CONFORMATIONALLY RESTRICTED 5-HT(3) RECEPTOR ANTAGONISTS
CLARK, RD
MILLER, AB
BERGER, J
REPKE, DB
WEINHARDT, KK
KOWALCZYK, BA
EGLEN, RM
BONHAUS, DW
LEE, CH
MICHEL, AD
SMITH, WL
WONG, EHF
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (18) : 2645 - 2657
[4] SYNTHESIS OF INDOLIC HETEROCYCLICS FROM CARBONYL DERIVATIVES OF INDOLE AND PYRROLE
DUPAS, G
DUFLOS, J
QUEGUINER, G
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (04) : 967 - 970
[5] Lewis acid-directed cyclocondensation of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine:: A new regioselective synthesis of oxygenated carbolines
Engler, TA
Wanner, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) : 2444 - 2457
[6] Evanno Y., 1998, [No title captured], Patent No. [WO 9815552, 9815552]
[7] Low-valent titanium induced indole formation: Syntheses of secofascaplysin, indolopyridocoline and an endothelin-receptor-antagonist
Furstner, A
Ernst, A
Krause, H
Ptock, A
[J]. TETRAHEDRON, 1996, 52 (21) : 7329 - 7344
[8] NEW HETEROCYCLIC RING-SYSTEMS - THE SYNTHESES OF 2H,3H,7H-IMIDAZO[1',2'/1,2]PYRIDO[4,3-B]INDOLES AND 2H,3H,4H,8H-PYRIMIDO[1',2'/1,2]PYRIDO[4,3-B]INDOLES
HARADA, K
SOMEYA, H
ZEN, S
[J]. HETEROCYCLES, 1994, 38 (08) : 1867 - 1880
[9] HECK RF, 1982, ORG REACTIONS, V27, P345
[10] NOVEL SPONGE-DERIVED AMINO-ACIDS .12. TRYPTOPHAN-DERIVED PIGMENTS AND ACCOMPANYING SESTERTERPENES FROM FASCAPLYSINOPIS-RETICULATA
JIMENEZ, C
QUINOA, E
ADAMCZESKI, M
HUNTER, LM
CREWS, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) : 3403 - 3410

← 1 2 3 →