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New, simple and efficient method for the synthesis of imidazo-azines by flash vacuum thermolysis of tert-butylimines of pyrimidine-2-, pyrazine-2-, quinoline-2-, quinoxaline-2- and isoquinoline-1-carbaldehydes

Abstract : 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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Submitted on : Thursday, June 29, 2017 - 9:45:51 AM
Last modification on : Friday, April 30, 2021 - 4:42:06 PM

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K. Justyna, Anna Chrostowska, S. Leśniak, Clovis Darrigan, Patrick Baylère, et al.. New, simple and efficient method for the synthesis of imidazo-azines by flash vacuum thermolysis of tert-butylimines of pyrimidine-2-, pyrazine-2-, quinoline-2-, quinoxaline-2- and isoquinoline-1-carbaldehydes. Journal of Analytical and Applied Pyrolysis, Elsevier, 2017, 125, pp.335-346. ⟨10.1016/j.jaap.2017.02.028⟩. ⟨hal-01549703⟩

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