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Paper | Regular issue | Vol 57, No. 6, 2002, pp.1033-1048
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9454
The Synthesis of 2,2-Disubstituted-3-nitrochromenes from Salicylaldehyde and 2,2-Disubstituted-1-nitroalkenes

Ming-Chung Yan, Yeong-Jiunn Jang, Wen-Yu Kuo, Zhijay Tu, Kao-Hsien Shen, Ting-Shen Cuo, Chuen-Her Ueng, and Ching-Fa Yao*

*Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei, 116, Taiwan, R.O.C.

Abstract

Reactions of salicylaldehyde (1) with β-nitrostyrenes (2), (4), and (6) in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) without the use of solvent at 40 °C gave high yields of the corresponding 3-nitrochromenes, respectively. Other conjugated nitroalkenes were also used to react with salicylaldehyde under the similar conditions and the yields of substituted 3-nitrochromenes were moderate to high. 96% of cis-3-nitro-4-hydroxyflavane (11) was isolated as sole stereoisomer when 1 reacted with 2-nitromethyleneadamantane (10) under similar condition. When the reaction temperature was increased to 90 °C, 11 underwent dehydration to generate 74% of the corresponding 3-nitrochromene (12).