CONVENIENT SYNTHESIS OF N-METHYL-3-(2-ETHENYLPHENYL)-1(2H)ISOQUINOLONES, KEY MODELS FOR THE ELABORATION OF THE BENZO[C]PHENANTHRIDINONE AND PHENANTHRIDINE SKELETONS

被引：13

作者：

COUTURE, A

CORNET, H

GRANDCLAUDON, P

机构：

[1] Laboratoire de Chimie Organique Physique associé au CNRS, Université des Sciences et Technologies de Lille

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(00)61461-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of N-methyl-3-(2-ethenylphenyl)-1(2H)-isoquinolones 1a-e have been prepared by base-induced intramolecular cyclization of N-(2-ethenylbenzoyl)-N,2-dimethylbenzamide derivatives 2a-e. The concomitant formation of the fused dihydro benzo[c]phenanthridinones 7a-e was also observed during this process.

引用

收藏

页码：8097 / 8100

页数：4

相关论文

共 19 条

[1]

Ager D. J., 1990, ORG REACTIONS, V38, P1, DOI DOI 10.1002/0471264180.0R038.01

[2] CHEMISTRY OF CRYPTOPINE .I. EPICRYPTOPINES [J].

DYKE, SF ;

BROWN, DW .

TETRAHEDRON, 1968, 24 (03) :1455-&

[3] CHEMICAL TRANSFORMATION OF PROTOBERBERINES .10. A NOVEL SYNTHESIS OF SANGUILUTINE AND DIHYDROSANGUILUTINE, FULLY AROMATIZED 2,3,7,8,10-PENTAOXYGENATED BENZO[C]PHENANTHRIDINE ALKALOIDS [J].

HANAOKA, M ;

KOBAYASHI, N ;

SHIMADA, KI ;

MUKAI, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (03) :677-681

[4] A NEW TOTAL SYNTHESIS OF OXYTERIHANINE [J].

HANAOKA, M ;

KOBAYASHI, N ;

MUKAI, C .

HETEROCYCLES, 1987, 26 (06) :1499-1501

[5] CHEMICAL TRANSFORMATION OF PROTOBERBERINES .9. A BIOMIMETIC SYNTHESIS OF OXYCHELERYTHRINE, DIHYDROCHELERYTHRINE, AND CHELERYTHRINE FROM BERBERINE [J].

HANAOKA, M ;

MOTONISHI, T ;

MUKAI, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12) :2253-2256

[6] NITRILE OXIDE CYCLOADDITION ROUTES TO 2-(ISOXAZOLYL)-BENZOATES AND 2-(1,2,4-OXADIAZOL-3-YL)BENZOATES [J].

HOWE, RK ;

SCHLEPPNIK, FM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (04) :721-726

[7] THE BENZOPHENANTHRIDINE ALKALOIDS [J].

KRANE, BD ;

FAGBULE, MO ;

SHAMMA, M ;

GOZLER, B .

JOURNAL OF NATURAL PRODUCTS, 1984, 47 (01) :1-43

[8]

MARTIN G, 1987, TETRAHEDRON LETT, P2407

[9] NUCLEOPHILIC AROMATIC-SUBSTITUTION ON ORTHO-(METHOXY)ARYLOXAZOLINES - CONVENIENT SYNTHESIS OF ORTHO-ALKYLIDENE ACIDS AND ORTHO-ALKYLDENE AND ORTHO-ARYLBENZOIC ACIDS [J].

MEYERS, AI ;

GABEL, R ;

MIHELICH, ED .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (07) :1372-1379

[10] PHOTOCYCLIZATION OF ENAMIDES .2. PHOTOCYCLIZATION OF N-BENZOYL ENAMINES OF 1-TETRALONE TO BENZO[C] [J].

NINOMIYA, I ;

NAITO, T ;

KIGUCHI, T ;

MORI, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (16) :1696-1701