Synthesis of 6‐Hydroxymethyl‐5,6‐dihydro‐4H‐1,2‐oxazines by One‐Pot‐Cyclization of Dilithiated Oximes with Epibromohydrin.

Abstract

Oxazine derivatives R 0595Synthesis of 6-Hydroxymethyl-5,6-dihydro-4H-1,2-oxazines by One-Pot-Cyclization of Dilithiated Oximes with Epibromohydrin. -Dilithiated oximes react regioselectively with epibromohydrin due to the higher nucleophilicity of the carbanion compared to the alkoxide within the dianion. The title compounds are isolated in moderate yields. -(ALBRECHT, U.; GERWIEN, K.; LANGER*, P.; Tetrahedron Lett. 46 (2005) 6, 1017-1019; Inst. Chem. Biochem., Ernst-Moritz-Arndt-Univ., D-17487 Greifswald, Germany; Eng.) -Mais 22-165