Reactivity of heterocyclic enaminones: Regioselective synthesis of polyfused indolones

被引：16

作者：

Blache, Y

Benezech, V

Chezal, JM

Boule, P

Viols, H

Chavignon, O

Teulade, JC

Chapat, JP

机构：

[1] Fac Pharm Montpellier, Lab Chim Organ Pharmaceut, EA 2414, F-34060 Montpellier, France

[2] UFR Pharm, Lab Chim Organ Pharmaceut, F-63001 Clermont Ferrand, France

[3] UFR Sci, Photochim Mol & Macromol Lab, F-63177 Clermont Ferrand, France

来源：

HETEROCYCLES | 2000年 / 53卷 / 04期

关键词：

photochemistry; electrocyclization; aminoquinoline; indoloquinoline; pyridocarbazole;

D O I：

10.3987/COM-99-8837

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photocyclization of heterocyclic enaminones to give partial hydrogenated derivatives of indolo[2,3-c]quinoline, pyrido[2,3-c]carbazole, and pyrido[4,3-a]carbazole is described: In addition, 3-[(5'-quinolinyl)-benzylamino]cyclohex-2-en-1-one and 3 -[(8'-quinolinyl) benzylamino]cyclohex-2-en-1-one undergo C-N bond cleavages and a benzyl migration on the C-6 and C-7 positions respectively.

引用

收藏

页码：905 / 916

页数：12

相关论文

共 25 条

[1] THE UTILIZATION OF TUNNEL EFFECTS FOR MECHANISTIC STUDIES OF HYDROGEN TRANSFER-REACTIONS [J].

BARON, U ;

BARTELT, G ;

EYCHMULLER, A ;

GRELLMANN, KH ;

SCHMITT, U ;

TAUER, E ;

WELLER, H .

JOURNAL OF PHOTOCHEMISTRY, 1985, 28 (02) :187-195

[2]

BLACHE Y, 1994, HETEROCYCLES, V38, P1241

[3] Application of the mercuric acetate-edetic acid oxidation method to the synthesis of 11-aza-1,2,3,4,5,6,7,12b-octahydroindolo[2,3-a]quinolizines [J].

Blache, Y ;

Hichour, M ;

Chavignon, O ;

Gueiffier, A ;

Teulade, JC ;

Dauphin, G ;

Chapat, JP .

HETEROCYCLES, 1997, 45 (01) :57-69

[4] Compared reactivity of heterocyclic enaminones: Photochemical and palladium catalyzed synthesis of 6,7,8,9-tetrahydro-5H-pyrido[3,2-b]ind-9-ones [J].

Blache, Y ;

SinibaldiTroin, ME ;

Voldoire, A ;

Chavignon, O ;

Gramain, JC ;

Teulade, JC ;

Chapat, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8553-8556

[5] Heterocyclic enaminones:: Photochemical synthesis of 6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-9-ones [J].

Blache, Y ;

Sinibaldi-Troin, ME ;

Hichour, M ;

Benezech, V ;

Chavignon, O ;

Gramain, JC ;

Teulade, JC ;

Chapat, JP .

TETRAHEDRON, 1999, 55 (07) :1959-1970

[6]

BRYSKIER A, 1988, PALUDISME MED

[7] NONOXIDATIVE PHOTOCYCLIZATION OF N-ARYL ENAMINES - FACILE SYNTHETIC ENTRY TO TRANS-HEXAHYDROCARBAZOLES [J].

CHAPMAN, OL ;

EIAN, GL ;

BLOOM, A ;

CLARDY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2918-&

[8] PHOTOCHEMICAL SYNTHESIS OF 2,3-DIHYDROINDOLES FROM N-ARYL ENAMINES [J].

CHAPMAN, OL ;

EIAN, GL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (19) :5329-&

[9] REACTIONS OF (VINYLIMINO)PHOSPHORANES AND RELATED-COMPOUNDS - ACCESS TO THE AZACARBOLINES AND APLYSINOPSINES [J].

CHAVIGNON, O ;

TEULADE, JC ;

ROCHE, D ;

MADESCLAIRE, M ;

BLACHE, Y ;

GUEIFFIER, A ;

CHABARD, JL ;

DAUPHIN, G .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6413-6418

[10] In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta [J].

Cimanga, K ;

DeBruyne, T ;

Pieters, L ;

Vlietinck, AJ .

JOURNAL OF NATURAL PRODUCTS, 1997, 60 (07) :688-691