Selective reactivity of sp3 and sp2 carbanions of 1-substituted 1,2,4-triazoles.: A comparative approach

被引:5
作者
Katritzky, AR [1 ]
Darabantu, M [1 ]
Aslan, DC [1 ]
Oniciu, DC [1 ]
机构
[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA
关键词
D O I
10.1021/jo9800659
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselectivity of lithiation reactions of 1-n-alkyl-, 1-allyl-, and 1-propargyl-1H-1,2,4-triazoles was studied in terms of the products formed by sequential treatment with BuLi and a range of electrophiles.
引用
收藏
页码:4323 / 4331
页数:9
相关论文
共 32 条
[1]  
[Anonymous], 2000, HDB HETEROCYCLIC CHE
[2]  
CHADWICK DJ, 1979, J CHEM SOC PERK T 1, P2845, DOI 10.1039/p19790002845
[3]  
CUBERES MR, 1985, SYNTHESIS-STUTTGART, P302
[4]  
DIEZBARRA E, 1994, HETEROCYCLES, V38, P1367
[5]   Partially delocalized allylic lithium compounds: Dynamics of inversion, 1,3 Li shift, and C-Li bond, exchange influence of the stereochemistry of solvation [J].
Fraenkel, G ;
Qiu, FY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (15) :3571-3579
[6]  
Garratt P. J., 1996, COMPREHENSIVE HETERO, V4, P127, DOI DOI 10.1016/B978-008096518-5.00080-0
[7]   STUDY ON ORGANOSILYL AZOLE SERIES .1. ACTION OF ALKYL-HALIDES, ACID-CHLORIDES AND HALOGENATED KETONES [J].
GASPARINI, JP ;
GASSEND, R ;
MAIRE, JC ;
ELGUERO, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 188 (02) :141-150
[8]  
HOMMES NJRV, 1991, J ORGANOMET CHEM, V409, P307
[9]  
HUMBURG G, 1982, LIEBIGS ANN CHEM, P1387
[10]   Asymmetric induction using chiral 1,2,4-triazole and benzimidazole derivatives [J].
Katritzky, AR ;
Aslan, DC ;
Leeming, P ;
Steel, PJ .
TETRAHEDRON-ASYMMETRY, 1997, 8 (09) :1491-1500