Type: Article
A novel one-pot three-component reaction: Synthesis of triheterocyclic 4H-pyrimido[2,1-b]benzazoles ring systems
Journal: Bioorganic and Medicinal Chemistry Letters (0960894X)Year: 2005/12/15Volume: 15Issue: 24Pages: 5553 - 5557
DOI:10.1016/j.bmcl.2005.08.101Language: English
Abstract
A novel one-pot three-component condensation reaction of an aldehyde, β-ketoester and 2-aminobenzimidazole or 2-aminobenzothiazole in 1,1,3,3-N,N,N′,N′-tetramethylguanidinium trifluoroacetate as an ionic liquid is described. During the course of this reaction 4H-pyrimido[2,1-b]benzimidazoles or 4H-pyrimido[2,1-b]benzothiazoles are formed in high yields at 100°C. The ionic liquid can be recovered conveniently and reused efficiently. © 2005 Elsevier Ltd. All rights reserved.
Author Keywords
2-Aminobenzimidazole2-Aminobenzothiazole4H-Pyrimido[2,1-b]benzimidazoles4H-Pyrimido[2,1-b]benzothiazolesMulticomponent
Other Keywords
BenzimidazolesBenzothiazolesHeterocyclic CompoundsModels, MolecularMolecular ConformationPyrimidinesThiazolesbenzene derivativebenzimidazole derivativebenzothiazole derivativeethyl 2 methyl 4 (4 bromophenyl) 4h pyrimido[2,1 b][1,3]benzothiazole 3 carboxylic acidethyl 2 methyl 4 (4 methoxyphenyl) 4,10 dihydropyrimido[2,1 a][1,3]benzimidazole 3 carboxylic acidethyl 2 methyl 4 (4 methoxyphenyl) 4h pyrimido[2,1 b][1,3]benzothiazole 3 carboxylic acidethyl 2 methyl 4 (4 nitrophenyl) 4,10 dihydropyrimido[2,1 a][1,3]benzimidazole 3 carboxylic acidethyl 2 methyl 4 (4 nitrophenyl) 4h pyrimido[2,1 b][1,3]benzothiazole 3 carboxylic acidethyl 2 methyl 4 (phenyl) 4,10 dihydropyrimido[2,1 a][1,3]benzimidazole 3 carboxylic acidethyl 2 methyl 4 (phenyl) 4h pyrimido[2,1 b][1,3]benzothiazole 3 carboxylic acidethyl 4 (4 methoxyphenyl) 2 phenyl 4,10 dihydropyrimido[2,1 a][1,3]benzimidazole 3 carboxylic acidethyl 4 (4 nitrophenyl) 2 phenyl 4,10 dihydropyrimido[2,1 a][1,3]benzimidazole 3 carboxylic acidethyl 4 (4 nitrophenyl) 2 phenyl 4h pyrimido[2,1 b][1,3]benzothiazole 3 carboxylic acidethyl 4 (phenyl) 2 phenyl 4h pyrimido[2,1 b][1,3]benzothiazole 3 carboxylic acidmethyl 2 methyl 4 (4 methoxyphenyl) 4h pyrimido[2,1 b][1,3]benzothiazole 3 carboxylic acidmethyl 2 methyl 4 (4 nitrophenyl) 4h pyrimido[2,1 b][1,3]benzothiazole 3 carboxylic acidmethyl 2 methyl 4 (phenyl) 4h pyrimido[2,1 b][1,3]benzothiazole 3 carboxylic acidpyrimidine derivativetrifluoroacetic acidunclassified drugarticledrug synthesisliquidpolymerizationtemperature