Add time:07/29/2019         Source:sciencedirect.com

Flash vacuum thermolysis reactions of N-(tert-butyl)-N-(pyrimidin-2-ylmethylidene)amine (1), N-(tert-butyl)-N-(pyrazin-2-ylmethylidene)amine (2), N-(tert-butyl)-N-(quinolin-2-ylmethylidene)amine (3), N-(tert-butyl)-N-(quinoxalin-2-ylmethylene)amine (4) and N-(tert-butyl)-N-(isoquinolin-2-ylmethylidene)amine (5) have been investigated. The formation of 3-methyl-imidazo[1,5-a]pyrimidine(6), 3-methyl-imidazo[1,5-a]pyrazine (7), 1-methyl-imidazo[1,5-a]quinoline (8), 3-methyl-imidazo[1,5-a] quinoxaline (9) and 3-methyl-imidazo[5,1-a]isoquinoline (10) as reaction products was observed. Excellent yields of imidazoazines from monocyclic imines 1 and 2 were found, whereas from bicyclic imines 3–5 slightly lower yields (50–75%) of the major products and formation of byproducts such as quinolone and isoquinoline were observed. These cyclizations were found to occur fully regioselectively onto the nitrogen atom of the adjacent ring. UV-photoelectron spectroscopy combined with FVT and quantum chemical calculations were applied for direct monitoring and characterization of the thermolysis products. The proposed mechanism of these reactions are substantiated by DFT calculations.

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