Synthesis of 4,4′-Dimethoxy-5,6,5′,6′-dimethenedioxy-2-alkyloxycarbonyl-2′-(4-substituted benzyl piperazin-1-yl)carbonyl-biphenyl

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (6): 691-696. Previous Articles Next Articles

4,4′-二甲氧基-5,6,5′,6′-二次甲二氧基-2-烷氧甲酰基-2′-(4-取代苄基哌嗪基-1)-甲酰基联苯的合成

程森祥^a,b, 王利敏^b, 常俊标^*,b, 屈凌波^a, 陈晓岚^a, 陈荣峰^b

^a郑州大学化学系郑州 450052
^b河南省科学院研究中心郑州 450002

收稿日期:2003-08-22 修回日期:2003-10-14 接受日期:2003-12-30 发布日期:2022-09-21
通讯作者: ^*E-mail: chsxchem@371.net
基金资助:
河南省自然科学基金(No. 0311022100)资助项目.

Synthesis of 4,4′-Dimethoxy-5,6,5′,6′-dimethenedioxy-2-alkyloxycarbonyl-2′-(4-substituted benzyl piperazin-1-yl)carbonyl-biphenyl

CHENG, Sen-Xiang^a,b, WANG, Li-Min^b, CHANG, Jun-Biao^*,b, QU, Ling-Bo^a, CHEN, Xiao-Lan^a, CHEN, Rong-Feng^b

^a Department of Chemistry, Zhengzhou University, Zhengzhou 450052
^b Center of Research, Henan Academy of Sciences, Zhengzhou 450002

Received:2003-08-22 Revised:2003-10-14 Accepted:2003-12-30 Published:2022-09-21

Abstract

The key intermediate, dimethyl 4,4′-dimethoxy-5,6,5′,6′-dimethenedioxy-biphenyl-2,2′-dicarboxylate (2), was synthesized in excellent yield from methyl 2-bromo-3,4-methenedioxy-5-methoxybenzoate through Ullmann-type coupling reaction in the presence of NiCl₂(PPh₃)₂/NaH/Zn/PPh₃, and then it was converted to 4,4′-dimethoxy-5,6,5′,6′-dimethenedioxy-2-alkyloxycarbonyl-biphenyl-2′-carboxylic acids (4a～4c) through hydrolysis, intramolecular dehydrolysisand single-esterification. The reactions of compounds 4a～4c with N-substituted benzyl piperazines afforded target compounds 5a～5n. The structures of these novel compounds were confirmed by ¹H NMR, IR, ESI-MS and elemental analysis.

Key words: biphenyl, Ullmann-type coupling, nickel bis(triphenylphosphine) dichloride, N-benzyl piperazine

Cite this article

CHENG, Sen-Xiang, WANG, Li-Min, CHANG, Jun-Biao, QU, Ling-Bo, CHEN, Xiao-Lan, CHEN, Rong-Feng. Synthesis of 4,4′-Dimethoxy-5,6,5′,6′-dimethenedioxy-2-alkyloxycarbonyl-2′-(4-substituted benzyl piperazin-1-yl)carbonyl-biphenyl[J]. Chinese Journal of Organic Chemistry, 2004, 24(6): 691-696.

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4,4′-二甲氧基-5,6,5′,6′-二次甲二氧基-2-烷氧甲酰基-2′-(4-取代苄基哌嗪基-1)-甲酰基联苯的合成

Synthesis of 4,4′-Dimethoxy-5,6,5′,6′-dimethenedioxy-2-alkyloxycarbonyl-2′-(4-substituted benzyl piperazin-1-yl)carbonyl-biphenyl

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