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Paper | Special issue | Vol 95, No. 2, 2017, pp.830-843
Published online, 25th November, 2016
DOI: 10.3987/COM-16-S(S)52
Synthesis of Multi-Substituted 1,4-Benzoxazine Using an Umpolung Reaction with 2-Oxo-1,4-benzoxazine-3-carboxylates

Takanori Tanaka, Isao Mizota, Kazuto Umezu, Akinori Ito, and Makoto Shimizu*

*Department of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurimamachiya-cho Tsu, Mie 514-8507, Japan


This report describes a one-pot synthesis of multi-substituted 1,4-benzoxazine derivatives by atom economical N,C-dialkylation reaction of 1,4-benzoxazine derivatives with various organozinc reagents and ketene silyl acetals (KSA).