期刊
TETRAHEDRON
卷 62, 期 36, 页码 8625-8635出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.06.066
关键词
MW-synthesis; regioselectivity; 6-prenylisoflavones; 3 '-iodochalcones; hypervalent iodine; wighteone; lupisoflavone; derrubone
Microwave-assisted oxidative rearrangement of 3'-iodotetraalkoxychalcones with hypervalent iodine such as [hydroxy(tosyloxy)iodo]benzene or [bis(trifluoroacetoxy)iodo] benzene, followed by microwave-mediated hydrolysis and in situ cyclization of the resultant acetals gave 6-iodotrialkoxyisoflavones. Pd(0)-catalyzed coupling reaction of the 6-iodoisoflavones with 2-methyl-3-butyn-2-of under microwave irradiation gave 6-alkynylisoflavones, whose hydrogenation gave the respective hydrates of wighteone, lupisoflavone and derrubone. Wighteone (1a), lupisoflavone (1b) and derrubone (1c) were obtained by dehydration of their respective hydrates under microwave irradiation. (c) 2006 Elsevier Ltd. All rights reserved.
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