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Paper | Regular issue | Vol 36, No. 4, 1993, pp.845-856
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6250
A Facile and Convenient Synthesis of Fluorine-containing Naphth[1,2-d][1,3]oxazines by Novel Cyclization of N,N-Dialkyl-2,4-bis(trifluoroacetyl)-1-naphthylamines

Etsuji Okada, Ryoichi Masuda, Masaru Hojo,* and Takeshi Tomifuji

*Department of Industrial Chemistry, Faculty of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan


N,N-Dialkyl-2,4-bis(trifluoroacetyl)-1-naphthylamines (1a-j) underwent acid catalyzed cyclization by trifluoroacetic acid or silica gel to give naphth[1,2-d][1,3]oxazines (2a-j) in excellent yields. Naphthylamines (1b, d, e, h-j) were found to perform this type of cyclization easily in refluxing butyronitrile or acetonitrile even in the absence of acids. Remarkably high regioselectivities were exhibited in the cyclization of unsymmetrically N,N-dialkyl-substituted naphthylamines (1g-j) and the corresponding naphth[1,2-d][1,3]oxazines (2g-j) were obtained in high yields.