Generation and reactions of 1-(2-indolyl)vinylcopper derivatives with pyridinium salts

被引：6

作者：

Bennasar, ML ^{[1
]}

Juan, C ^{[1
]}

Roca, T ^{[1
]}

Monerris, M ^{[1
]}

Bosch, J ^{[1
]}

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 51期

关键词：

copper and compounds; tin and compounds; pyridinium salts; indole;

D O I：

10.1016/S0040-4020(01)01065-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-(2-Indolyl)vinylstannane 1b has been transmetallated into both the corresponding HO mixed cyanocuprate and the Cu-catalysed organomagnesium reagent, and the reactivity of these species towards N-alkyl-3-acylpyridinium salts 8 and 17 has been tested. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：10125 / 10131

页数：7

共 35 条

[1] A CONVENIENT METHOD FOR THE REGIOSELECTIVE SYNTHESIS OF 4-ALKYL(ARYL)PYRIDINES USING PYRIDINIUM SALTS [J].

AKIBA, K ;

ISEKI, Y ;

WADA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (07) :1994-1999

[2] Conjugate addition of organocuprates to chiral bicyclic δ-lactams.: Enantioselective synthesis of cis-3,4-disubstituted and 3,4,5-trisubstituted piperidines [J].

Amat, M ;

Pérez, M ;

Llor, N ;

Bosch, J ;

Lago, E ;

Molins, E .

ORGANIC LETTERS, 2001, 3 (04) :611-614

[3] RING-FORMATION FROM ALLYLSTANNANES AND VINYLSTANNANES INITIATED BY TREATMENT WITH BUTYL-LITHIUM [J].

BARBERO, A ;

CUADRADO, P ;

GONZALEZ, AM ;

PULIDO, FJ ;

RUBIO, R ;

FLEMING, I .

TETRAHEDRON LETTERS, 1992, 33 (39) :5841-5842

[4] Total synthesis of (+)-papuamine: An antifungal pentacyclic alkaloid from a marine sponge, Haliclona sp. [J].

Barrett, AGM ;

Boys, ML ;

Boehm, TL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :685-699

[5] INSITU CUPRATE FORMATION VIA TRANSMETALATION BETWEEN VINYLSTANNANES AND HIGHER-ORDER CYANOCUPRATES [J].

BEHLING, JR ;

BABIAK, KA ;

NG, JS ;

CAMPBELL, AL ;

MORETTI, R ;

KOERNER, M ;

LIPSHUTZ, BH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2641-2643

[6]

Belle DD, 1996, TETRAHEDRON, V52, P11361

[7] NUCLEOPHILIC-ADDITION OF 2-INDOLYLACYL ANION EQUIVALENTS TO N-ALKYLPYRIDINIUM SALTS [J].

BENNASAR, ML ;

ZULAICA, E ;

BOSCH, J .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2835-2841

[8] Synthesis of 3,5-diacyl-4-phenyl-1,4-dihydropyridines [J].

Bennasar, ML ;

Juan, C ;

Bosch, J .

TETRAHEDRON LETTERS, 1998, 39 (50) :9275-9278

[9] Addition of organocopper reagents to N-alkylpyridinium salts.: A flexible access to polysubstituted dihydropyridines [J].

Bennasar, ML ;

Juan, C ;

Bosch, J .

TETRAHEDRON LETTERS, 2001, 42 (04) :585-588

[10]

Bhandari K. S., 1971, CAN J CHEM, V49, P2354

← 1 2 3 4 →