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

被引：25

作者：

Bennasar, ML ^{[1
]}

Juan, C ^{[1
]}

Bosch, J ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 04期

关键词：

acylation; copper and compounds; pyridines; pyridinium salts;

D O I：

10.1016/S0040-4039(00)02006-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of a series of organocopper (alkyl, vinyl, allyl, and ethynyl) reagents to 3-acyl-N-alkylpyridinium salts, followed by acylation of the intermediate 1,4- or 1,2-dihydropyridines with trichloroacetic anhydride has been studied. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：585 / 588

页数：4

共 25 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]

[Anonymous], 1996, Adv. Nitrogen Heterocycl

[3] 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

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

Bennasar, ML ;

Juan, C ;

Bosch, J .

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

[5] NUCLEOPHILIC-ADDITION OF 2-ACETYLINDOLE ENOLATES TO PYRIDINIUM SALTS - ACYLATION OF THE INTERMEDIATE DIHYDROPYRIDINES [J].

BENNASAR, ML ;

VIDAL, B ;

BOSCH, J .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4280-4286

[6]

COMINS DL, 1984, HETEROCYCLES, V22, P151

[7] REGIOSELECTIVE ADDITION OF GRIGNARD-REAGENTS TO 1-ACYLPYRIDINIUM SALTS - A CONVENIENT METHOD FOR THE SYNTHESIS OF 4-ALKYL(ARYL)PYRIDINES [J].

COMINS, DL ;

ABDULLAH, AH .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (22) :4315-4319

[8] Asymmetric synthesis of the Lycopodium alkaloid, Na-acetyl-Nb-methylphlegmarine [J].

Comins, DL ;

Libby, AH ;

Al-awar, RS ;

Foti, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2184-2185

[9] Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric syntheses of indolizidine alkaloids (-)-205A, (-)-207A, and (-)-235B [J].

Comins, DL ;

LaMunyon, DH ;

Chen, XH .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8182-8187

[10] 1,4-DIHYDROPYRIDINES - EFFECTS OF CHIRALITY AND CONFORMATION ON THE CALCIUM-ANTAGONIST AND CALCIUM AGONIST ACTIVITIES [J].

GOLDMANN, S ;

STOLTEFUSS, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12) :1559-1578

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