期刊
TETRAHEDRON LETTERS
卷 46, 期 33, 页码 5515-5519出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.06.058
关键词
conjugate reduction; chroman-4-ones; chromones; flavones; rearrangement
3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.
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