Cycloaddition of nitrile oxides to aza-analogues of phenanthrene

被引:9
作者
Corsaro, A [1 ]
Librando, V [1 ]
Chiacchio, U [1 ]
Pistarà, V [1 ]
Rescifina, A [1 ]
机构
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
关键词
D O I
10.1016/S0040-4020(98)00556-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mesitonitrile oxide, but not benzonitrile oxide, adds to ate-analogues of phenanthrene to give low yields of monocycloadducts. Only phenanthridine reacts with the two nitrile oxides affording phenanthridinone. 4,7-phenanthroline also gives some other minor products among which the bisadduct to a pyridine ring was isolated. The reactivity of aza-analogues under examination is discussed in terms of FMO approximation. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9187 / 9194
页数:8
相关论文
共 21 条
[1]   CROSSED BISADDUCTS IN THE REACTION OF PYRIDINE WITH 2 DIFFERENT NITRILE OXIDES [J].
ALBINI, FM ;
DEFRANCO, R ;
BANDIERA, T ;
CARAMELLA, P ;
CORSARO, A ;
PERRINI, G .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (03) :757-761
[2]  
[Anonymous], TRENDS HETEROCYCL CH
[3]  
[Anonymous], 1985, ADV ORG CHEM
[4]  
BIANCHI G, 1972, J CHEM SOC P1, P1712
[5]   SELECTIVITY IN CYCLOADDITIONS .7. CYCLOADDITIONS OF NITRILE OXIDES TO THIOPHENE AND BENZO[B]THIOPHENE - REGIOCHEMISTRY [J].
CARAMELLA, P ;
CELLERINO, G ;
GRUNANGER, P ;
ALBINI, FM ;
RECELLERINO, MR .
TETRAHEDRON, 1978, 34 (24) :3545-3551
[6]   SELECTIVITY IN CYCLO-ADDITIONS, .15. ADDITION OF PYRIDINE AND ISOQUINOLINE TO BENZOYLCARBONITRILE OXIDE [J].
CARAMELLA, P ;
BANDIERA, T ;
ALBINI, FM ;
GAMBA, A ;
CORSARO, A ;
PERRINI, G .
TETRAHEDRON, 1988, 44 (15) :4917-4925
[7]  
Caramella P., 1984, 1 3 DIPOLAR CYCLOADD, V1, P291
[8]   1,3-dipolar cycloadditions of polycyclic aromatic hydrocarbons with nitrile oxides under microwave irradiation in the absence of solvent [J].
Corsaro, A ;
Chiacchio, U ;
Librando, V ;
Fisichella, S ;
Pistara, V .
HETEROCYCLES, 1997, 45 (08) :1567-1572
[9]   1,3-dipolar cycloaddition reactions of polycyclic aromatic hydrocarbons with 3,5-dichloro-2,4,6-trimethyl- and 2,4,6-trimethylbenzonitrile oxide. [J].
Corsaro, A ;
Librando, V ;
Chiacchio, U ;
Pistara, V .
TETRAHEDRON, 1996, 52 (40) :13027-13034
[10]  
CORSARO A, 1995, J CHEM RES-S, P352