[3+2] Cycloaddition of Oxaziridines with Nitriles: Synthesis of 2,3-Dihydro-1,2,4-Oxadiazoles

被引:18
作者
Troisi, Luigino [1 ]
Ronzini, Ludovico [1 ]
Rosato, Francesca [1 ]
Videtta, Valeria [1 ]
机构
[1] Univ Salento, Dipartimento Sci & Tecnol Biol Ambientali, I-73100 Lecce, Italy
关键词
cycloaddition; oxaziridines; nitriles; 2,3-dihydro-1,2,4 oxadiazoles; heterocycles; 1,3-DIPOLAR CYCLOADDITION; NITRONES; DERIVATIVES; SUBSTITUENT; ORGANONITRILES;
D O I
10.1055/s-0029-1217186
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and simpler preparation of 2,3-dihydro-1,2,4 oxadiazoles by synchronous [3+2] cycloaddition between oxaziridines and nitriles is presented.
引用
收藏
页码:1806 / 1808
页数:3
相关论文
共 31 条
[1]   Nitro and related compounds [J].
Adams, JP ;
Box, DS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (07) :749-764
[2]   Nitro and related compounds [J].
Adams, JP ;
Paterson, JR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (22) :3695-3705
[3]  
[Anonymous], CHEM HETEROCYCL COMP
[4]   One-pot synthesis of novel derivatives of spiro-[6H-indolo [2,1-b]quinazoline-6,3′-[1,2,4]oxadiazoline] [J].
Azizian, J ;
Madani, M ;
Souzangarzadeh, S .
SYNTHETIC COMMUNICATIONS, 2005, 35 (06) :765-768
[5]   4,5-DIHYDROISOXAZOLE AND 4,5-DIHYDRO-1,2,4-OXADIAZOLE DERIVATIVES FROM CYCLOADDITION REACTIONS OF NITRILE OXIDES TO ALKYL N-(DIPHENYLMETHYLENE)-ALPHA,BETA-DEHYDROAMINO ACIDS [J].
BALSAMINI, C ;
SPADONI, G ;
BEDINI, A ;
TARZIA, G ;
LANFRANCHI, M ;
PELLINGHELLI, MA .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (06) :1593-1598
[6]   1,3-dipolar cycloaddition of nitrones to free and coordinated nitriles: Routes to control the synthesis of 2,3-dihydro-1,2,4-oxadiazoles [J].
Bokach, N. A. ;
Kukushkin, V. Yu. .
RUSSIAN CHEMICAL BULLETIN, 2006, 55 (11) :1869-1882
[7]  
Chimirri A, 1996, FARMACO, V51, P125
[8]   1,3-dipolar cycloaddition of α-phenyl-N-tert-butylnitrone (PBN) to dichloro- and dibromo-malononitrile, chlorotricyanomethane and tetracyanomethane.: Structure of products and kinetics of their formation [J].
Eberson, L ;
McCullough, JJ ;
Hartshorn, CM ;
Hartshorn, MP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (01) :41-47
[9]   Synthesis of stable isoxazolines by [3+2] cycloaddition of oxaziridines with alkynes [J].
Fabio, Marilena ;
Ronzini, Ludovico ;
Troisi, Luigino .
TETRAHEDRON, 2008, 64 (22) :4979-4984
[10]   Synthesis of new 3,5-diarylisoxazolidines by cycloaddition of oxaziridines and alkenes [J].
Fabio, Marilena ;
Ronzini, Ludovico ;
Troisi, Luigino .
TETRAHEDRON, 2007, 63 (52) :12896-12902