QUINAZOLINES AND 1,4-BENZODIAZEPINES .42. PHOTOCHEMISTRY OF SOME N-OXIDES

被引:36
作者
FIELD, GF
STERNBAC.LH
机构
[1] Chemical Research Department, Hoffmann-La Roche Inc., Nutley
关键词
D O I
10.1021/jo01276a027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Quinazoline 3-oxides 1 are photoisomerized to benzo [f]-1,3,5-oxadiazepines 2. 6-Chloro-2-methyl-4-phenylquinazoline 1-oxide (4) gives 1-acetyl-5-chloro-3-phenylindazole (6) on irradiation. 7-Chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine 3-oxide (9) gives a mixture of 9-chloro-5-methylamino-2-phenyl-4H-benzo[g]-1,3,6-oxadiazocine (11) and 1-benzoyl-7-chloro-1,2-dihydro-3-methylaminoquinoxaline (12a). These transformations are believed to proceed by rearrangement of the oxaziridines formed as primary isomerization products. © 1968, American Chemical Society. All rights reserved.
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页码:4438 / &
相关论文
共 16 条
[1]  
Abernethy J. L., 1964, J CHEM EDUC, V41, P53
[2]  
Bell S. C., 1964, J ORG CHEM, V29, P506
[3]   PHOTOCHEMICAL STUDIES .X. ON PHOTOLYSIS OF 2,3-DIPHENYLQUINOZALINE N-OXIDE TO 2,4-DIPHENYLBENZ[D]-1,3,5-OXADIAZEPINE . AN NMR STUDY [J].
BUCHARDT, O ;
FEENEY, J .
ACTA CHEMICA SCANDINAVICA, 1967, 21 (05) :1399-&
[4]  
BUCHARDT O, 1967, TETRAHEDRON LETT, P2741
[5]  
BUCHARDT O, 1966, TETRAHEDRON LETT, P6221
[6]   PHOTOCHEMICAL STUDIES .8. FORMATION OF BENZ[D]-1,3-OXAZEPINES IN PHOTOLYSIS OF QUINOLINE-N-OXIDES IN SOLUTION [J].
BUCHARDT, O ;
JENSEN, B ;
LARSEN, IK .
ACTA CHEMICA SCANDINAVICA, 1967, 21 (07) :1841-&
[7]  
DZIEWONSKI K, 1936, CA 29724, V30
[8]  
DZIEWONSKI K, 1935, B INT ACAD POLON M A, V333
[9]  
EDWARD JT, 1956, J CHEM SOC, P222
[10]   NITRONES .3. PHOTOLYSIS OF CYCLIC NITRONES [J].
KAMINSKY, LS ;
LAMCHEN, M .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (24) :2295-&