Lewis acid-directed cyclocondensation of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine:: A new regioselective synthesis of oxygenated carbolines

被引：46

作者：

Engler, TA ^{[1
]}

Wanner, J ^{[1
]}

机构：

[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 08期

关键词：

D O I：

10.1021/jo9916176

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis acid-directed cyclocondensations of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine are reported. Benzofurans are obtained with BF3. OEt2 as a promoter, whereas use of excess amounts of TiCl4:Ti(OiPr)(4) leads to tetrahydrocarbolines. The latter reactions provide expedient routes to oxygen-substituted tetrahydrocarbolines and carbolines. As applications of this new methodology, the preparations of 1-[3-(dimethylamino)propyl] amino-7-methoxy- and 1-[3-(dimethylamino)propyl]amino-7,8-dimethoxy-5H-pyrido[4,3-b]indoles are described.

引用

收藏

页码：2444 / 2457

页数：14

相关论文

共 80 条

[1] ANTIPSYCHOTIC ACTIVITY OF SUBSTITUTED GAMMA-CARBOLINES [J].

ABOUGHARBIA, M ;

PATEL, UR ;

WEBB, MB ;

MOYER, JA ;

ANDREE, TH ;

MUTH, EA .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (10) :1818-1823

[2] PSYCHOTROPIC AGENTS - SYNTHESIS AND ANTIPSYCHOTIC ACTIVITY OF SUBSTITUTED BETA-CARBOLINES [J].

ABOUGHARBIA, M ;

PATEL, UR ;

MOYER, JA ;

MUTH, EA .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (06) :1100-1105

[3]

ADAMS R, 1958, B SOC CHIM FR, P23

[4]

[Anonymous], COMPREHENSIVE ORGANI

[5] Potent, selective tetrahydro-beta-carboline antagonists of the serotonin 2B (5HT(2B)) contractile receptor in the rat stomach fundus [J].

Audia, JE ;

Evrard, DA ;

Murdoch, GR ;

Droste, JJ ;

Nissen, JS ;

Schenck, KW ;

Fludzinski, P ;

Lucaites, VL ;

Nelson, DL ;

Cohen, ML .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (14) :2773-2780

[6] MULTIDENTATE LEWIS-ACIDS - ADDUCTS OF MONODENTATE AND BIDENTATE TITANIUM TRICHLOROALKOXIDES WITH KETONES [J].

BACHAND, B ;

WUEST, JD .

ORGANOMETALLICS, 1991, 10 (06) :2015-2025

[7]

BAKER BJ, 1996, ALKALOIDS CHEM BIOL, V10

[8] NEW WAY TO VINYLIC ETHERS FROM ACETALS [J].

BARBOT, F ;

MIGINIAC, P .

HELVETICA CHIMICA ACTA, 1979, 62 (05) :1451-1457

[9] 1-AMINO-SUBSTITUTED 4-METHYL-5H-PYRIDO[4,3-B]INDOLES (GAMMA-CARBOLINES) AS TRICYCLIC ANALOGS OF ELLIPTICINES - A NEW CLASS OF ANTINEOPLASTIC AGENTS [J].

BISAGNI, E ;

NGUYEN, CH ;

PIERRE, A ;

PEPIN, O ;

DECOINTET, P ;

GROS, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (02) :398-405

[10] REGIOCONTROLLED NUCLEOPHILIC-ADDITION TO SELECTIVELY ACTIVATED PARA-QUINONE DIIMINES - ALTERNATIVE PREPARATION OF A KEY INTERMEDIATE EMPLOYED IN THE PREPARATION OF THE CC-1065 LEFT-HAND SUBUNIT [J].

BOGER, DL ;

ZARRINMAYEH, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1379-1390

← 1 2 3 4 5 6 7 8 →