NEW SYNTHESIS OF DIARYLALKYNES FROM 1-(ARYLMETHYL)BENZOTRIAZOLES AND ARYLIDENEAMINES

被引:13
作者
KATRITZKY, AR
GORDEEV, MF
机构
[1] Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 11期
关键词
D O I
10.1039/p19920001295
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Michael addition of lithio derivatives 2 of 1-(arylmethyl)benzotriazoles 1 to arylideneamines 3-5 gave the corresponding 1-(benzotriazol-1-yl)-2-anilino (or tosylamino)-1,2-diarylethanes 6-8. The latter were shown to undergo a double elimination reaction under the action of Bu(t)OK in DMF to afford diarylalkynes in high yields.
引用
收藏
页码:1295 / 1298
页数:4
相关论文
共 34 条
[1]   A NEW GENERAL-SYNTHESIS OF ALIPHATIC AND TERMINAL ALKYNES - FLASH VACUUM PYROLYSIS OF BETA-OXOALKYLIDENETRIPHENYLPHOSPHORANES [J].
AITKEN, RA ;
ATHERTON, JI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1140-1141
[2]  
AVILA L, 1983, HETEROCYCLES, V20, P1787
[3]   REACTIONS WITH PHOSPHINE ALKYLENES .42. A SEQUENCE FOR THE PREPARATION OF ACETYLENES STARTING FROM CARBOXYLIC CHLORIDES AND PHOSPHORUS YLIDES VIA 1,2-DIKETONES [J].
BESTMANN, HJ ;
KUMAR, K ;
KISIELOWSKI, L .
CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (06) :2378-2382
[4]  
BUECHI G, 1979, J ORG CHEM, V44, P4116
[5]   SIMPLE PROCEDURE FOR ELABORATION OF CARBONYL-COMPOUNDS INTO HOMOLOGOUS ALKYNES [J].
COLVIN, EW ;
HAMILL, BJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (08) :869-874
[6]  
CRAM DJ, 1965, FUNDAMENTALS CARBANI, P90
[7]   A CONVENIENT ROUTE TO ALKYNES VIA PHASE-TRANSFER CATALYSIS (APPLICATIONS OF PHASE-TRANSFER CATALYSIS .19. [J].
DEHMLOW, EV ;
LISSEL, M .
TETRAHEDRON, 1981, 37 (09) :1653-1658
[8]  
FLETCHER IJ, 1978, ADV HETEROCYCL CHEM, V23, P171
[9]   THE PYROLYSIS OF 1-BENZYLBENZOTRIAZOLE AND SOME HOMOLOGUES THEREOF [J].
GIBSON, MS .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (APR) :1076-1078
[10]   DIAZOETHENES - THEIR ATTEMPTED SYNTHESIS FROM ALDEHYDES AND AROMATIC KETONES BY WAY OF THE HORNER-EMMONS MODIFICATION OF THE WITTIG REACTION - A FACILE SYNTHESIS OF ALKYNES [J].
GILBERT, JC ;
WEERASOORIYA, U .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1837-1845