1,2,5-oxadiazole (Furazan) derivatives from benzoylnitromethane and dipolarophiles in the presence of DABCO: Structure and intermediates

被引:22
作者
Cecchi, Luca
De Sarlo, Francesco
Faggi, Cristina
Machetti, Fabrizio
机构
[1] Univ Florence, Dipartimento Chim Organ U Schiff, Ist Chim Composti Organo Met, CNR, I-50019 Florence, Italy
[2] Univ Florence, CRIST, Ctr Interdipartimental Cristallog Strutturale, I-50019 Florence, Italy
关键词
cycloaddition; DABCO; heterocycles; nitro compounds; rearrangement;
D O I
10.1002/ejoc.200600039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Furazan (1,2,5-oxadiazole) derivatives are obtained along with isoxazolines from the reaction of benzoylnitromethane with dipolarophiles in the presence of DABCO. Furazans are shown to derive from the intermediate dibenzoylfuroxan (3,4-dibenzoyl-1, 2,5-oxadiazole-5-oxide) and dipolarophiles under hydrolytic conditions. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
引用
收藏
页码:3016 / 3020
页数:5
相关论文
共 19 条
[1]  
ALTAFURRAHMAN M, 1972, TETRAHEDRON LETT, V13, P3469
[2]   SIR97:: a new tool for crystal structure determination and refinement [J].
Altomare, A ;
Burla, MC ;
Camalli, M ;
Cascarano, GL ;
Giacovazzo, C ;
Guagliardi, A ;
Moliterni, AGG ;
Polidori, G ;
Spagna, R .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119
[3]   4-PNEHYL-4H-PYRAZOLO[3,4-C] FURAZANS . REACTIONS OF 3,4-DIACYLFUROXANS WITH PHENYLHYDRAZINE AND WITH ANILINE [J].
BERTELSO.RC ;
GLANZ, KD ;
MCQUAIN, DB .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (03) :317-&
[4]   NEW FUROXAN CHEMISTRY .2. CHEMISTRY OF ACYL NITRILE OXIDES GENERATED INSITU BY THERMOLYSIS OF DIACYLFUROXANS [J].
BRITTELLI, DR ;
BOSWELL, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02) :316-320
[5]   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
[6]   Isoxazoline derivatives from activated primary nitrocompounds and tertiary diamines [J].
Cecchi, L ;
De Sarlo, F ;
Machetti, F .
TETRAHEDRON LETTERS, 2005, 46 (46) :7877-7879
[7]   THE CHEMISTRY OF FULMINIC ACID REVISED [J].
DESARLO, F ;
GUARNA, A ;
BRANDI, A ;
GOTI, A .
TETRAHEDRON, 1985, 41 (22) :5181-5185
[8]  
Juhász-Tóth É, 2002, EUR J ORG CHEM, V2002, P3055
[9]   Synthesis of hydroximoyl chlorides from aldoximes and benzyltrimethylammonium tetrachloroiodate (BTMA ICl4) [J].
Kanemasa, S ;
Matsuda, H ;
Kamimura, A ;
Kakinami, T .
TETRAHEDRON, 2000, 56 (08) :1057-1064
[10]   Microwave assisted rupture of furoxans to nitrile oxides and intermolecular capture by dipolarophiles [J].
Karmakar, D ;
Prajapati, D ;
Sandhu, JS .
SYNTHETIC COMMUNICATIONS, 1998, 28 (13) :2415-2420