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One-pot synthesis of iodine-substituted 1,4-oxazepines

Zora, Metin
A facile one-pot method for the synthesis of iodine-substituted 1,4-oxazepines is reported. When reacted with ZnCl2 and I-2 in DCM at 40 degrees C, N-propargylic beta-enaminones, prepared by the conjugate addition of propargylamine to alpha,beta-alkynic ketones, underwent 7-exo-dig cyclization by zinc chloride and concomitant reaction with molecular iodine to afford 2-(iodomethylene)-2,3-dihydro-1,4-oxazepines in good to high yields. This cyclization was found to occur with broad scope of substrates and high tolerance of functional groups. The resulting iodine-containing 1,4-oxazepines can be further elaborated to more complex structures by subsequent cross-coupling reactions, which may provide a platform for biological studies. (C) 2018 Elsevier Ltd. All rights reserved.