Synlett 2006(17): 2791-2794  
DOI: 10.1055/s-2006-950267
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Characterization of [1]Benzopyrano[4,3-d][1,3]benzooxazocin-13-one and its Derivatives

Jen-Fei Wang, Yuan-Xiu Liao, Pei-Yu Kuo, Yung-Her Gau, Ding-Yah Yang*
Department of Chemistry, Tunghai University, 181, Taichung-Kang Rd. Sec. 3, Taichung 40704, Taiwan
Fax: +886(4)23590426; e-Mail: yang@thu.edu.tw;
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Publication History

Received 21 June 2006
Publication Date:
09 October 2006 (online)

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Abstract

This work describes the efficient synthesis of functionalized cleft molecules 6, 6a, 16, 16a, 17, 19 and 20 derived from benzopyrano[4,3-d][1,3]benzooxazocin-13-one. X-ray crystal structure analysis of compounds 6a and 16a revealed that the cleft angles of the planes of the benzopyran moiety and the p-methoxybenzene ring are 109.4° and 108.6°, respectively. The conformation of the aromatic ring at the bridgehead of 16, 16a and 20 is restricted by the gem-dimethyl groups on the C-9 position and the methyl group on the nitrogen atom in the ring.