HYDROXYLATION OF 5H-3-OXO-2,3,6,7,8,9-HEXAHYDROIMIDAZO[1,2-A]AZEPINE DERIVATIVES BY MOLECULAR-OXYGEN

被引:7
作者
CAMPAGNA, F
CAROTTI, A
CASINI, G
机构
[1] Dipartimento Farmaco-Chimico, University of Bari, Bari, 70126
关键词
D O I
10.1002/jhet.5570270723
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
O-Methylcaprolactim 3 reacts in hot dimethylsulfoxide with alpha-amino acids 4 to give 5H-3-oxo-2,3,6,7,8,9-hexahydroimidazo[1,2-a]azepines 6 and, unexpectedly, hydroxylated derivatives 7a,c and 8c. The structures of the hydroxylated compounds have been elucidated by spectroscopic means and, when necessary, further confirmed by an independent unequivocal synthesis. The formation of 7 as well as the isomerization of 7c to 8c are discussed in detail.
引用
收藏
页码:1973 / 1977
页数:5
相关论文
共 17 条
[1]   A SIMPLE SYNTHESIS OF HETEROCYCLIC RING-SYSTEMS CONTAINING THE 1,3-OXAZINE NUCLEUS [J].
ALTOMARE, C ;
CAROTTI, A ;
CASINI, G ;
FERAPPI, M .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (03) :777-779
[2]  
ALTOMARE C, 1985, HETEROCYCLES, V23, P1933
[3]   HETEROCYCLIC STEROIDS .2. SYNTHESIS OF SOME SPIRO DERIVATIVES OF 7,8-DIAZA-11-OXASTEROIDS [J].
ALTOMARE, C ;
CAROTTI, A ;
CAMPAGNA, F .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (06) :1751-1752
[4]   SYNTHESIS AND COGNITION ACTIVATING PROPERTIES OF SOME MONOCYCLIC AND BICYCLIC LACTAM DERIVATIVES [J].
ALTOMARE, C ;
CAROTTI, A ;
CASINI, G ;
CELLAMARE, S ;
FERAPPI, M ;
GAVUZZO, E ;
MAZZA, F ;
PANTALEONI, G ;
GIORGI, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (11) :2153-2158
[5]   CHEMICAL AND CATALYTIC REDUCTIVE ISOMERIZATION OF [1,3]OXAZINO[2,3-A]ISOQUINOLINES TO [1,3]OXAZINO[3,2-B]ISOQUINOLINES [J].
CAMPAGNA, F ;
CAROTTI, A ;
CASINI, G .
HETEROCYCLES, 1988, 27 (01) :245-252
[6]   SYNTHESIS OF 12-MONO-SUBSTITUTED AND DISUBSTITUTED 8-AZA-11-OXASTEROIDS [J].
CAMPAGNA, F ;
ALTOMARE, C ;
CAROTTI, A ;
CASINI, G ;
FERAPPI, M .
STEROIDS, 1986, 47 (4-5) :307-320
[7]   SYNTHESIS OF NEW HETEROCYCLIC RING-SYSTEMS - INDENO[2,1-B]-BENZO[G]INDOLIZINE AND INDENO[1',2'-5,4]PYRROLO[2,1-A]PHTHALAZINE [J].
CAMPAGNA, F ;
CAROTTI, A ;
CASINI, G ;
MACRIPO, M .
HETEROCYCLES, 1990, 31 (01) :97-107
[8]   ONE-STEP SYNTHESIS OF AN INDENO-INDOLIZINE NUCLEUS [J].
CAROTTI, A ;
CASINI, G ;
GAVUZZO, E ;
MAZZA, F .
HETEROCYCLES, 1985, 23 (07) :1659-1669
[9]  
CAROTTI A, 1981, FARMACO-ED SCI, V36, P146
[10]   REVERSIBLE CYCLIZATION OF N-(3-HYDROXY-1-ALKENYL)PYRIDINIUM SALTS TO PYRIDOOXAZINES [J].
CAROTTI, A ;
CASINI, G ;
FERAPPI, M ;
CINGOLANI, GM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (07) :1577-1584