Synthesis of new 1H-imidazoles via reactions of 3(,5)-(di)chloro-2H-1,4-(benz)oxazin-2-ones with α-aminoketones

Add time:07/26/2019    Source:sciencedirect.com

3,5-Dichloro-2H-1,4-oxazin-2-ones 1 and 3-chloro-2H-1,4-benzoxazin-2-ones 2 react with α-aminoketones to yield bi- and tricyclic imidazo-fused intermediates via an intramolecular cyclisation reaction. Reaction of these lactone intermediates with various nucleophiles generates new substituted 1H-imidazoles useful for pharmacological screening. Reactions of compounds 1 with β-amino-alcohols followed by treatment with SOCl2 provides 2,3-dihydro-8H-imidazo[2,1-c]-1,4-oxazin-8-ones but lactone cleavage resulted in the formation of some unidentified decomposition products.

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