One-step synthesis of alkyl 2-chloropyrimido[1,2-a]benzimidazole-3-carboxylates under catalyst-free: combined experimental and computational studies

[Display omitted] An efficient method for the preparation of pyrimido[1,2-a]benzimidazole derivatives utilizing squaric acid dichloride has been developed at room temperature without catalyst. This method provided a rapid synthesis of pyrimido[1,2-a]benzimidazole system. The result indicates that th...

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Bibliographic Details
Published in:Tetrahedron letters 2015-09, Vol.56 (36), p.5071-5075
Main Authors: Liu, Yang, Xia, Guoming, Luo, Chao, Sun, Jianqi, Ye, Benfei, Yuan, Yanli, Wang, Hongming
Format: Article
Language:English
Subjects:
Catalyst-free
DFT calculation
Pyrimido[1,2-a]benzimidazole
Squaric acid dichloride
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Summary:[Display omitted] An efficient method for the preparation of pyrimido[1,2-a]benzimidazole derivatives utilizing squaric acid dichloride has been developed at room temperature without catalyst. This method provided a rapid synthesis of pyrimido[1,2-a]benzimidazole system. The result indicates that those expeditious reactions could be carried out only in the presence of alcohols, affording the corresponding alkyl 2-chloropyrimido[1,2-a]benzimidazole-3-carboxylates. Furthermore, the yield of products seems to be closely relevant to the steric hindrance of the added alcohols. On the basis of experimental and theoretical analyses, a plausible mechanism has been proposed and corroborated through DFT calculations for exploring a practical way to efficiently synthesize those highly versatile substituted homologs.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.07.050