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A new facile approach to the synthesis of 3-methylthio-substituted furans, pyrroles, thiophenes, and related derivatives

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成果类型:
期刊论文
作者:
Yin, Guodong;Wang, Zihua;Chen, Aihua;Gao, Meng;Wu, Anxin*吴安心);...
通讯作者:
Wu, Anxin
作者机构:
[Wu, Anxin; Yin, Guodong; Gao, Meng; Wang, Zihua; Chen, Aihua] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
[Pan, Yuanjiang] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China.
通讯机构:
[Wu, Anxin] C
Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
语种:
英文
期刊:
JOURNAL OF ORGANIC CHEMISTRY
ISSN:
0022-3263
年:
2008
卷:
73
期:
9
页码:
3377-3383
机构署名:
本校为第一且通讯机构
院系归属:
化学学院
摘要:
(Chemical Equation Presented) 2-(Methylthio)-1,4-diaryl-2-butene-1,4-dione (3) are prepared from readily available aryl methyl ketones in the presence of copper(II) oxide, iodine, and dimethyl sulfoxide. The success of the cross-coupling reaction of 4-chloroacetophenone with 2-acetylthiophene confirms a proposed self-sorting tandem reaction mechanism. Both Z- and E-isomers of compound 3 are readily converted into the corresponding 3-methylthio 2,5-diaryl furan 7 in good yield through a domino process involving the reduction of the double bond followed by the Paal-Knorr furan synthesis. Meanwhi...

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