TITLE:
Reaction of Nitrilimines with 2-Aminopicoline, 3-Amino-1,2,4-Triazole, 5-Aminotetrazole and 2-Aminopyrimidine
AUTHORS:
Rami Y. Morjan, Basam S. Qeshta, Hussein T. Al-Shayyah, John M. Gardiner, Basam A. Abu-Thaher, Adel M. Awadallah
KEYWORDS:
Nitrilimines, Picolines, Imidazo[1, 2-a]Pyridine, Triazoles, Tetrazoles, Pyrimidines
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.4 No.3,
September
17,
2014
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.