3H-AZEPINES AND RELATED SYSTEMS .4. PREPARATION OF 3H-AZEPIN-2-ONES AND 6H-AZEPINO[2,1-B]QUINAZOLIN-12-ONES BY PHOTOINDUCED RING EXPANSIONS OF ARYL AZIDES

被引：38

作者：

LAMARA, K ^{[1
]}

SMALLEY, RK ^{[1
]}

机构：

[1] UNIV SALFORD,DEPT CHEM & APPL CHEM,SALFORD M5 4WT,LANCS,ENGLAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 12-13期

关键词：

D O I：

10.1016/S0040-4020(01)96138-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photolysis of a series of p-substituted phenyl azides (p-X-C6H4N3; X = CO2Me, CO2Et, CN, CF3, SO2NH2, CO2CHPh2, COMe, CHO, and NO2) in 1:1 (nu/nu) THF-water solution produces, in the majority of cases, a 5-substituted-3H-azepine-2-one. In a like manner, 3H-azepin-2-one-3-carboxylates can be prepared from 5-substituted-2-azidobenzoates, providing the 5-substituent is electron-withdrawing. 3H-Azepin-2-one mono- and di-carboxylic acids, the former in admixture with decarboxylated material, and 6H-azepino[2,1-b]quinazolin-12-ones, are obtained by irradiation of 2-azidobenzoic acid and of 5-azidoisophthalic acid, respectively. The mode of formation of the azepino-quinazolinones is discussed.

引用

页码：2277 / 2290

页数：14

共 42 条

[1] 3H-AZEPINES AND RELATED SYSTEMS .3. MONO-2-ALKOXY-3H-AZEPINE-3-CARBOXYLATES AND BIS-2-ALKOXY-3H-AZEPINE-3-CARBOXYLATES AND -3-CARBOXAMIDES BY PHOTOLYSIS OF MONO-ORTHO-AZIDOBENZOYL AND DI-ORTHO-AZIDOBENZOYL DERIVATIVES OF GLYCOLS AND DIAMINES - SOME ACYCLIC CROWN ETHER ANALOGS [J].

AZADIARDAKANI, M ;

SALEM, SM ;

SMALLEY, RK ;

PATEL, DI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (06) :1121-1126

[2]

AZADIARDAKANI M, 1983, J CHEM SOC P1, P2501

[3] REACTIONS OF 2-DIALKYLAMINO-3H-AZEPINES WITH OXIDANTS AND ELECTROPHILES [J].

BATORI, S ;

GOMPPER, R ;

MEIER, J ;

WAGNER, HU .

TETRAHEDRON, 1988, 44 (11) :3309-3318

[4] COMPARATIVE STUDY OF PHOTOLYTIC DECOMPOSITIONS OF 2-AZIDOACETOPHENONE AND 3-METHYLANTHRANIL [J].

BERWICK, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (22) :5780-&

[5]

BRETSCHNEIDER H, 1950, MONATSH CHEM, V81, P970

[6] EXAMINATION OF UTILITY OF PHOTOGENERATED REAGENTS BY USING ALPHA-CHYMOTRYPSIN [J].

BRIDGES, AJ ;

KNOWLES, JR .

BIOCHEMICAL JOURNAL, 1974, 143 (03) :663-668

[7] RING-EXPANSION OF AZIDOBENZENESULFONAMIDES AND AZIDOBENZAMIDES [J].

BROWN, TB ;

LOWE, PR ;

SCHWALBE, CH ;

STEVENS, MFG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10) :2485-2490

[8]

CARROLL SE, 1977, TETRAHEDRON LETT, P3175

[9] 1-AZA-1,2,4,6-CYCLOHEPTATETRAENE [J].

CHAPMAN, OL ;

LEROUX, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) :282-285

[10] DIDEHYDROAZEPINES FROM THE PHOTOLYSIS OF PHENYL AZIDE AND 3-SUBSTITUTED AND 4-SUBSTITUTED PHENYL AZIDES ISOLATED IN LOW-TEMPERATURE MATRICES [J].

DONNELLY, T ;

DUNKIN, IR ;

NORWOOD, DSD ;

PRENTICE, A ;

SHIELDS, CJ ;

THOMSON, PCP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (02) :307-310

← 1 2 3 4 5 →