Solid-phase synthesis of 3-alkylamino-1 2,4-triazoles

被引:27
作者
Makara, GM [1 ]
Ma, Y [1 ]
Margarida, L [1 ]
机构
[1] NeoGenesis Pharmaceut, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ol025821i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A solid-phase synthesis of trisubstituted 3-alkylamino-1,2,4-triazoles has been developed. The synthesis utilizes immobilized N-acyl-1H-benzotriazole-1-carboximidamides as key intermediates. Cyclization with hydrazines under mild conditions furnishes the title compounds with regioselectivity and high purity.
引用
收藏
页码:1751 / 1754
页数:4
相关论文
共 18 条
[1]  
Akahoshi F., 1995, WO Patent, Patent No. 9503286
[2]   Solid-phase synthesis of 1,4-benzodiazepine-2,5-diones. Library preparation and demonstration of synthesis generality [J].
Boojamra, CG ;
Burow, KM ;
Thompson, LA ;
Ellman, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1240-1256
[3]  
Clitherow J. W., 1989, European Patent, Patent No. [367484, EP 367484]
[4]  
Fauchere J.-L., 2000, European Patent, Patent No. [EP 1044970, 1044970]
[5]  
Gyorgydeak Z, 1998, HETEROCYCLES, V48, P1395
[6]  
Hartmann M., 1985, BIOCIDE POLYM, P195
[7]   Di(benzotriazol-1-yl)methanimine: A new reagent for the synthesis of tri- and tetrasubstituted guanidines [J].
Katritzky, AR ;
Rogovoy, BV ;
Chassaing, C ;
Vvedensky, V .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :8080-8082
[8]   Synthesis of substituted 4(6)-amino-1,3,5-triazin-2-ones and-1,3,5-triazin-2-thiones [J].
Katritzky, AR ;
Rogovoy, BV ;
Vvedensky, VY ;
Hebert, N ;
Forood, B .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6797-6799
[9]  
Katritzky AR, 2001, SYNTHESIS-STUTTGART, P897
[10]   Synthesis of 1,2,4-triazole-functionalized solid support and its use in the solid-phase synthesis of trisubstituted 1,2,4-triazoles [J].
Katritzky, AR ;
Qi, M ;
Feng, DM ;
Zhang, GF ;
Griffith, MC ;
Watson, K .
ORGANIC LETTERS, 1999, 1 (08) :1189-1191