Novel cycloadducts from the 1,3-dipolar cycloaddition reactions of triazolium-1-imide 1,3-dipoles

被引:0
作者
Sheridan, M [1 ]
James, P [1 ]
Healy, C [1 ]
机构
[1] Dublin City Univ, Sch Chem Sci, Dublin 9, Ireland
关键词
1,3-dipolar cycloaddition; N-sulfonyl imines; benzyne;
D O I
10.3998/ark.5550190.0004.711
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A range of imidazo-1,2,3-triazoles were synthesised by the 1,3-dipolar cycloaddition of triazolium-1-imides with N-sulfonyl imines. Oxazolo-1,2,3-triazoles were identified as side products of this reaction. Benzyne was also used as a 1,3-dipolarophile in the cycloaddition reaction, resulting in a range of tricyclic triazolo indoles.
引用
收藏
页码:110 / 120
页数:11
相关论文
共 21 条
[1]   HETEROCYCLEN DURCH DIENSYNTHESE .2. N-[BUTYLOXYCARBONYLMENTHYLEN]-P-TOLUOLSULFONAMID EIN NEUES DIENOPHIL ZUR DARSTELLUNG VON PYRIDIN- PIPERIDEIN- UND PIPERIDIN-DERIVATEN DURCH DIELS-ALDER-SYNTHESE [J].
ALBRECHT, R ;
KRESZE, G .
CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (05) :1431-&
[2]  
ALBRECHT R, 1964, CHEM BER, V12, P949
[3]   REASSIGNMENT OF STRUCTURES OF DIHYDRO-V-TETRAZINES .2. MECHANISM OF OXIDATION OF DIACYLHYDRAZONES [J].
ALEXANDROU, NE .
TETRAHEDRON, 1966, 22 (04) :1309-+
[4]  
ANGADIYAVAR CS, 1971, TETRAHEDRON LETT, P633
[5]   A FACILE PROCEDURE FOR THE SYNTHESIS OF N-(TOSYL) IMINO-2 ACETIC-ACID ESTERS, IMPORTANT ENOPHILES FOR THE DIRECT SYNTHESIS OF EXOTIC ALPHA-AMINO-ACIDS [J].
BAILLARGE, M ;
LEGOFFIC, F .
SYNTHETIC COMMUNICATIONS, 1987, 17 (13) :1603-1606
[6]  
Boger D. L., 1987, HETERO DIELS ALDER M
[7]   INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF N-SULFONYL ALPHA,BETA-UNSATURATED IMINES - A GENERAL-APPROACH TO IMPLEMENTATION OF THE 4-PI PARTICIPATION OF 1-AZA-1,3-BUTADIENES IN DIELS-ALDER REACTIONS [J].
BOGER, DL ;
CORBETT, WL ;
CURRAN, TT ;
KASPER, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1713-1729
[9]   SUBSTITUTED BICYCLIC AND TRICYCLIC OXAZOLO[4,5-D]-1,2,3-TRIAZOLE SYSTEMS - RING EXPANSIONS TO 1,3,4,5-OXATRIAZINES AND RING CONTRACTIONS TO 1,2,3-TRIAZASPIROALKANE DERIVATIVES [J].
BUTLER, RN ;
OSHEA, DF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (19) :2797-2800
[10]   A NEW FUSED TRICYCLIC TETRA-AZA[4.3.3.01,6]DODECENE SYSTEM - SUBSTITUTED 3,3A,4,5,6,6A-HEXAHYDROPYRROLO[2,3-D]-1,2,3-TRIAZOLES FROM THE REACTION OF ACRYLONITRILE WITH CIS-1,2-BIS(ARENEAZO)ETHYLENES AND A REASSESSMENT OF 1,3-CYCLOADDITION PRODUCTS [J].
BUTLER, RN ;
CUNNINGHAM, D ;
JAMES, JP ;
MCARDLE, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (14) :762-763