STEREOSELECTIVE SYNTHESIS OF 4-PIPERIDONE AND 4-AMINOTETRAHYDROPYRIDINE DERIVATIVES BY THE IMINO DIELS-ALDER REACTION OF 2-AMINO-1,3-BUTADIENES

被引：35

作者：

BARLUENGA, J

AZNAR, F

VALDES, C

CABAL, MP

机构：

[1] Departamento de Química Organometálica, Facultad de Química, Universidad de Oviedo

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 12期

关键词：

D O I：

10.1021/jo00064a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Amino-4-(alkoxymethyl)-1,3-butadienes react smoothly with nonactivated aldimines derived from aromatic aldehydes in the presence of ZnCl2 as Lewis acid giving rise, with good yields and very high stereoselectivity, to substituted 4-aminotetrahydropyridines which upon hydrolysis yield 4-piperidone derivatives. Moreover, the stereochemistry of the cyclization process depends on the nature of the N-substituent of the imine.

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页码：3391 / 3396

页数：6

相关论文

共 23 条

[1] NEW 4-(HETEROANILIDO)PIPERIDINES, STRUCTURALLY RELATED TO THE PURE OPIOID AGONIST FENTANYL, WITH AGONIST AND OR ANTAGONIST PROPERTIES [J].

BAGLEY, JR ;

WYNN, RL ;

RUDO, FG ;

DOORLEY, BM ;

SPENCER, HK ;

SPAULDING, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (03) :663-671

[2] CATALYTIC AMINOMERCURATION REACTIONS OF 3-ALKEN-1-YNES - AN IMPROVED METHOD FOR THE SYNTHESIS OF 2-AMINO-1,3-BUTADIENES AND 1-AZA-1,3-BUTADIENES [J].

BARLUENGA, J ;

AZNAR, F ;

VALDES, C ;

CABAL, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6166-6171

[3] A NEW 2-AMINOBUTA-1,3-DIENE DERIVATIVE AND ITS UTILITY AS A BUILDING BLOCK IN HETERO-CYCLIZATION AND CARBO-CYCLIZATION PROCESSES [J].

BARLUENGA, J ;

AZNAR, F ;

CABAL, MP ;

CANO, FH ;

DELACONCEPCION, M ;

FOCESFOCES, MD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (18) :1247-1249

[4]

BOGER DL, 1987, HETERO DIELS ALDER M, P35

[5] REINVESTIGATION OF THE STEVENS REARRANGEMENT OF 1,3,4-TRIMETHYL-1-(3,4,5-TRIMETHOXYBENZYL)-1,2,5,6-TETRAHYDROPYRIDINIUM CHLORIDE [J].

BOSCH, J ;

DOMINGO, A ;

LOPEZ, F ;

RUBIRALTA, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (02) :241-244

[6] A NOVEL SYNTHESIS OF 2-ARYL-4-PIPERIDONES BY MANNICH CYCLIZATION OF IMINOKETALS [J].

BOSCH, J ;

RUBIRALTA, M ;

MORAL, M ;

VALLS, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (03) :595-605

[7] SILICON-ASSISTED SYNTHESIS OF BETA-LACTAMS [J].

COLVIN, EW ;

MCGARRY, D ;

NUGENT, MJ .

TETRAHEDRON, 1988, 44 (13) :4157-4172

[8] ASYMMETRIC AZA-DIELS-ALDER REACTION MEDIATED BY CHIRAL BORON REAGENT [J].

HATTORI, K ;

YAMAMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3264-3265

[9] CYCLOADDITION REACTIONS OF CARBOHYDRATE-DERIVATIVES .3. A NEW ROUTE TO SWAINSONINE ANALOGS [J].

HERCZEGH, P ;

KOVACS, I ;

SZILAGYI, L ;

ZSELY, M ;

SZTARICSKAI, F ;

BERECIBAR, A ;

OLESKER, A ;

LUKACS, G .

TETRAHEDRON LETTERS, 1992, 33 (22) :3133-3136

[10] SYNTHETIC 1,4-DISUBSTITUTED-1,4-DIHYDRO-5H-TETRAZOL-5-ONE DERIVATIVES OF FENTANYL - ALFENTANIL (R-39209), A POTENT, EXTREMELY SHORT-ACTING NARCOTIC ANALGESIC [J].

JANSSENS, F ;

TORREMANS, J ;

JANSSEN, PAJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) :2290-2297