THE ASYMMETRIC-SYNTHESIS OF 1-ALKYL-2,3,4,5-TETRAHYDRO-BENZAZEPINES AND BENZO[BETA]-1-AZABICYCLO[5,3,1]DECANES

被引：47

作者：

MEYERS, AI

HUTCHINGS, RH

机构：

[1] Department of Chemistry, Colorado State University, Fort Collins

来源：

TETRAHEDRON | 1993年 / 49卷 / 09期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4020(01)80537-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The metalation-alkylation of benzazepine formamidines gives high yields and good diastereoselectivity of 1-substituted derivatives. Removal of the chiral auxiliary leads to the title compounds in 84-96% ee and represents the first chiral benzazepines prepared via asymmetric synthesis.

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页码：1807 / 1820

页数：14

相关论文

共 19 条

[1] SYNTHESIS OF NOVEL TETRAHYDROBENZAZEPINONES [J].

BUSACCA, CA ;

JOHNSON, RE .

TETRAHEDRON LETTERS, 1992, 33 (02) :165-168

[2] SYNTHESIS AND INVESTIGATION OF THE BETA-ADRENOCEPTOR AGONIST AND PLATELET ANTIAGGREGATORY PROPERTIES OF 1,7,8-TRISUBSTITUTED "2,3,4,5-TETRAHYDRO-1H-2-BENZAZEPINE ANALOGS OF TRIMETOQUINOL [J].

CLARK, MT ;

CHANG, J ;

NAVRAN, SS ;

HUZOORAKBAR ;

MUKHOPADHYAY, A ;

AMIN, H ;

FELLER, DR ;

MILLER, DD .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (02) :181-185

[3]

DICKMAN DA, 1989, ORG SYNTH, V67, P52

[4]

FUSHIMI T, 1979, HETEROCYCLES, V12, P1311

[5] BRIDGED-RING NITROGEN-COMPOUNDS .10. SYNTHESIS OF BRIDGED 3-BENZAZEPINE DERIVATIVES AS CONFORMATIONALLY RESTRICTED DOPAMINE ANALOGS [J].

GENTLES, RG ;

MIDDLEMISS, D ;

PROCTOR, GR ;

SNEDDON, AH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1423-1431

[6] A REGIOSELECTIVE SYNTHESIS OF 8,9-DICHLORO-2,3,4,5-TETRAHYDRO-1H-2-BENZAZEPINE (LY134046), A POTENT PHENYLETHANOLAMINE N-METHYLTRANSFERASE INHIBITOR [J].

GRUNEWALD, GL ;

PARADKAR, VM .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (01) :59-60

[7]

HJELTE NS, 1964, SCAND CHIM ACTA, V1, P191

[8]

LAZARUS S, 1971, SCAND CHIM ACTA, V8, P495

[9] PHOTOCHEMICAL-SYNTHESIS OF TETRAHYDROBENZAZEPINES VIA INTRAMOLECULAR STILBENE-AMINE PHOTOADDITION [J].

LEWIS, FD ;

REDDY, GD .

TETRAHEDRON LETTERS, 1992, 33 (30) :4249-4252

[10]

Lwowski W., 1984, COMPREHENSIVE HETERO, V7