Reaction of Nitrilimines with 2-Aminopicoline, 3-Amino-1,2,4-Triazole, 5-Aminotetrazole and 2-Aminopyrimidine

Rami Y. Morjan¹, Basam S. Qeshta¹, Hussein T. Al-Shayyah¹, John M. Gardiner², Basam A. Abu-Thaher¹, Adel M. Awadallah^1*

¹Department of Chemistry, Islamic University of Gaza, Gaza, Palestine.
²Manchester Institute of Biotechnology, School of Chemistry and EPS, The University of Manchester, Manchester, UK.

DOI: 10.4236/ijoc.2014.43023                

Abstract

The reaction of picoline derivatives 3-6 with hydrazonoylhalide 1a produced imidazo[1,2-a]pyridines 7-10, while the reaction of the same picoline derivatives with hydrazonoylhalide 1b afforded imidazo[1,2-a]pyridine-2-ones 11-13. The reaction of 1b, c with 3-amino-1,2,4-triazole 14 produced the acyclic adducts 18 and 19, respectively. Reaction of 1b, 1c with 5-aminotetrazole 20 produced the acyclic products 23 and 24, respectively. Finally, the reaction of 1b with 4, 6-dimethyl-2-aminopyrimidine 27 afforded compound 29 rather than its isomeric structure 28. The structure of the products was confirmed by the different spectroscopic analytical methods including IR, MS, ¹HNMR and ¹³CNMR.

Keywords

Nitrilimines, Picolines, Imidazo[1, 2-a]Pyridine, Triazoles, Tetrazoles, Pyrimidines

Conflicts of Interest

The authors declare no conflicts of interest.

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