A novel photochemical synthesis of 5,6-dihydro-4H-1,2-oxazines by DCA-sensitized irradiation of gamma,delta-unsaturated oximes

被引：12

作者：

Armesto, D ^{[1
]}

Austin, MA ^{[1
]}

Griffiths, OJ ^{[1
]}

Horspool, WM ^{[1
]}

Carpintero, M ^{[1
]}

机构：

[1] UNIV DUNDEE,DEPT CHEM,DUNDEE DD1 4HN,SCOTLAND

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 24期

关键词：

D O I：

10.1039/cc9960002715

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

On DCA-sensitized irradiation 6,6-diphenylhex-5-en-2-one oxime 5a, 5,5-diphenylpent-4-enal oxime 5b and 2,2-dimethyl-5-phenylpent-4-enal oxime 5c undergo a novel photochemical cyclization yielding 3-methyl-6-diphenylmethyl-5,6-dihydro-4H-1,2-oxazine 9a, 6-diphenylmethyl-5,6-dihydro-4H-1,2-oxazine 9b and 6-benzyl-4,4-dimethyl-5,6-dihydro-4H-1,2-oxazine 9c, respectively.

引用

收藏

页码：2715 / 2716

页数：2

相关论文

共 14 条

[1] PHOTOLYSIS OF 2-AZIDOPYRIDINE 1-OXIDES - A CONVENIENT SYNTHESIS OF 1,2-OXAZINES [J].

ABRAMOVITCH, RA ;

DUPUY, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (02) :36-37

[2] A STUDY OF THE COMPETITION BETWEEN THE DI-PI-METHANE AND THE AZADI-PI-METHANE PROCESSES IN 2-VINYL-BETA,GAMMA-UNSATURATED OXIME DERIVATIVES - THE NOVEL AZADI-PI-METHANE REACTIVITY OF GAMMA-UNSATURATED OXIMES [J].

ARMESTO, D ;

ORTIZ, MJ ;

RAMOS, A ;

HORSPOOL, WM ;

MAYORAL, EP .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8115-8124

[3]

Armesto D, 1995, RECL TRAV CHIM PAY B, V114, P514

[4] THE AZA-DI-PI-METHANE REARRANGEMENT OF BETA,GAMMA-UNSATURATED OXIMES [J].

ARMESTO, D ;

RAMOS, A ;

MAYORAL, EP .

TETRAHEDRON LETTERS, 1994, 35 (22) :3785-3788

[5]

BONDIELL WE, 1985, J MED CHEM, V56, P1452

[6]

CURPHEY TJ, 1975, J ORG CHEM, V40, P607, DOI 10.1021/jo00893a014

[7] ACID-CATALYZED REARRANGEMENT OF 3-ACYL-6-ALKOXY-5,6-DIHYDRO-4H-1,2-OXAZINES - A ROUTE TO 3-ALKOXYPYRIDINE 1-OXIDES [J].

GILCHRIST, TL ;

ISKANDER, GM ;

YAGOUB, AK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2769-2773

[8] SYNTHESIS AND PHARMACOLOGICAL PROPERTIES OF NEW 6-AMINO-3,6-DIHYDRO-2H-1,2-OXAZINES [J].

KVITA, V ;

SAUTER, H ;

SCHIEWECK, K ;

STANEK, J .

ARCHIV DER PHARMAZIE, 1988, 321 (05) :263-264

[9] REACTIONS OF NITROSONIUM HEXAFLUOROPHOSPHATE WITH SOME OLEFINIC COMPOUNDS IN ACETONITRILE - ONE-STEP SYNTHESIS OF 4H-5,6-DIHYDRO-1,2-OXAZINES [J].

LEE, GH ;

LEE, JM ;

JEONG, WB ;

KIM, K .

TETRAHEDRON LETTERS, 1988, 29 (35) :4437-4440

[10] A NOVEL ROUTE TO DELTA,EPSILON-UNSATURATED-ALPHA-KETOCARBOXYLIC ACID-ESTERS VIA RING-OPENING OF 6-TRIMETHYLSILYLMETHYL-5,6-DIHYDRO-4H-1,2-OXAZINES [J].

NAKANISHI, S ;

HIGUCHI, M ;

FLOOD, TC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (01) :30-31