Highly efficient synthesis of triazolo[1,2-a]indazole-triones and novel spiro triazolo[1,2-a]indazole-tetraones under solvent-free conditions

被引：99
作者：
Hasaninejad, Alireza [1 ]
Zare, Abdolkarim [2 ]
Shekouhy, Mohsen [1 ]
机构：
[1] Persian Gulf Univ, Fac Sci, Dept Chem, Bushehr 75169, Iran
[2] PNU, Dept Chem, Bushehr 1698, Iran
来源：
TETRAHEDRON | 2011年 / 67卷 / 02期
关键词：
Combinatorial chemistry; Multi-component reaction; PEG-SO3H; Urazole; Triazolo[1,2-a]indazole-triones; Spiro triazolo[1,2-a]indazole-tetraone; BIGINELLI DIHYDROPYRIMIDINE SYNTHESIS; HETEROGENEOUS CATALYTIC-SYSTEM; SILICA SULFURIC-ACID; CARBONYL-COMPOUNDS; ATOM ECONOMY; MILD; CONDENSATION; DERIVATIVES; CHEMISTRY; LIBRARIES;
D O I：
10.1016/j.tet.2010.11.029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new, convenient, and high yielding procedure for the synthesis of triazolo[1,2-a]indazole-triones by the condensation reaction between dimedone, aryl aldehydes, and ueazoles in the presence of a catalytic amount of sulfonated polyethylene glycol (PEG-SO3H) as a highly stable and reusable eco-friendly degradable polymeric catalyst is described under solvent-free conditions. This procedure has also been applied successfully for the synthesis of novel Spiro triazolo[1,2-a]indazole-tetraones. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：390 / 400
页数：11
相关论文
共 45 条
  • [1] Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents
    Abdel-Rahman, AH
    Keshk, EM
    Hanna, MA
    El-Bady, SM
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) : 2483 - 2488
  • [2] Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
  • [3] 2-E
  • [4] Banfi L., 2005, Organic Reactions, V65, P1, DOI [10.1002/0471264180.or065.01, DOI 10.1002/0471264180.0R065.01]
  • [5] Banfi L, 2005, MULTICOMPONENT REACTIONS, P1, DOI 10.1002/3527605118.ch1
  • [6] A novel three-component method for the synthesis of triazolo[1,2-a]indazole-triones
    Bazgir, Ayoob
    Seyyedhamzeh, Mozhdeh
    Yasaei, Zahra
    Mirzaei, Peiman
    [J]. TETRAHEDRON LETTERS, 2007, 48 (50) : 8790 - 8794
  • [7] Bredow B. V., 1974, Ger. Offen., Patent No. [2343347, 2343347 A1]
  • [8] Ciardelli F., 1996, MACROMOLECULE METAL
  • [9] Craig P.N., 1991, COMPREHENSIVE MED CH, V8
  • [10] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
12345