Base-catalyzed, efficient synthesis of 5-substituted 3,6-dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones

被引:14
作者
Zhao, JF [1 ]
Xie, C [1 ]
Ding, MW [1 ]
He, HW [1 ]
机构
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China
来源
SYNTHESIS-STUTTGART | 2005年 / 15期
关键词
pyrimidines; imides; cyclizations; aza-Wittig reactions; heterocycles; guanines;
D O I
10.1055/s-2005-872077
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aromatic isocyanates, reacted with secondary amines or ROH to give 5-dialkylamino or 5-alkoxy 7H-1,2,3 -triazolo [4,5-d] pyrimidin-7-ones 4 in the presence of a catalytic amount of EtONa in a mixed solvent (CH2Cl2-ROH). Reactions of 2 with phenols in presence of catalytic potassium carbonate in MeCN gave 5-aryloxy-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones 4 in satisfactory yields.
引用
收藏
页码:2544 / 2548
页数:5
相关论文
共 21 条
[1]   AMINOPYRIMIDINES AND DERIVATIVES .15. SYNTHESIS OF 3-GLYCOSYL-VIC-TRIAZOLO-(4,5-D) PYRIMIDINES [J].
ASENJO, RA ;
SAMPEDRO, MM ;
MONTIEL, MN ;
ALONSO, MR ;
MELGAREJO, CR ;
RODRIGO, AS .
NUCLEOSIDES & NUCLEOTIDES, 1984, 3 (02) :207-219
[2]  
Blanco JM, 1999, CHEM PHARM BULL, V47, P1314
[3]  
Chen MD, 2000, CHINESE J ORG CHEM, V20, P357
[4]  
Chen MD, 2003, HETEROCYCL COMMUN, V9, P395
[5]   A new and facile method for synthesis of Aza-Wittig reagents under microwave irradiation [J].
Chen, MD ;
Yuan, GP ;
Yang, SY .
SYNTHETIC COMMUNICATIONS, 2000, 30 (07) :1287-1294
[6]   SYNTHESIS OF 8-AZAPURINES GLYCOSIDES STARTING FROM 1-AZIDOGLYCOSIDES [J].
CHRETIEN, F ;
GROSS, B .
TETRAHEDRON, 1982, 38 (01) :103-112
[7]   Application of bis(iminophosphorane) in heterocyclic synthesis:: New entries to symmetrically or unsymmetrically substituted thieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-diones [J].
Ding, MW ;
Xu, SZ ;
Zhao, JF .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) :8366-8371
[8]   New efficient synthesis of 1,2,4-triazolo[5,1-b]quinazolin-9(3H)-ones via a tandem aza-Wittig/heterocumulene-mediated annulation [J].
Ding, MW ;
Chen, YF ;
Huang, NY .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (18) :3872-3878
[9]   New facile synthesis of imidazo[2,1-b]-1,3,4-thiadiazol-5(6H)-ones via aza-Wittig reaction [J].
Ding, MW ;
Fu, BQ ;
Cheng, L .
SYNTHESIS-STUTTGART, 2004, (07) :1067-1071
[10]   New efficient synthesis of 2-substituted 5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones [J].
Ding, MW ;
Yang, SJ ;
Zhu, J .
SYNTHESIS-STUTTGART, 2004, (01) :75-79