DBU-Catalyzed Benzannulation towards Stilbene and Biaryl Derivatives from Acyclic Amides with Methyl Coumalate

Qin, Jialiang1; Ke, Mingji1; Cuo, Deji1; Xin, Shangping1; Xue, Yongbo2; Zhan, Ruoting1; Huang, Huicai1,3

2023-11-01

10.1002/ejoc.202300711

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   影响因子和分区

1434-193X

1099-0690

["The DBU-catalyzed benzylation of 1H-benzotriazole amides with methyl coumalate is demonstrated for the synthesis of stilbenes and biaryl derivatives. The transformation involves the base-catalyzed Michael addition of methyl coumalate to the 6 pi-electrocyclic ring opening decarboxylation aromatization. Furthermore, the novel 2-phenylnaphthalene derivatives showed potent anti-proliferative and anti-invasive activities against H1299 cells.","An efficient and environmentally friendly reaction with 1H-benzotriazoleamide and methyl coumalate using DBU as catalyst to obtain arene derivatives in good yields is reported.+image"]

antitumor benzannulation biaryl derivatives methyl coumalate stilbenes

SCI

英语

通讯

This work was supported financially by the National Natural Science Foundation of China (22001048, 21977120), the Pearl River Talents Recruitment Program of Guangdong Province (2017GC010361), Guangdong Provincial Special Fund For Modern Agriculture Industr["22001048","21977120"] ; National Natural Science Foundation of China[2017GC010361] ; Pearl River Talents Recruitment Program of Guangdong Province[2023KJ148] ; Guangdong Provincial Special Fund For Modern Agriculture Industry Technology Innovation Teams[202102020215] ; Science and Technology Program of Guangzhou[JCYJ20200109142215045] ; Key Basic Research Program of the Science, Technology and Innovation Commission of Shenzhen Municipality[2020B121201002]

Chemistry

Chemistry, Organic

WOS:001105419900001

WILEY-V C H VERLAG GMBH

CHEMISTRY

2-s2.0-85177473427

Web of Science

1.Guangzhou Univ Chinese Med, Sch Pharmaceut Sci, Key Lab Chinese Med Resource Lingnan, Minist Educ, Guangzhou 510006, Peoples R China
2.Sun Yat Sen Univ, Sch Pharmaceut Sci Shenzhen, Shenzhen 518107, Peoples R China
3.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China

Qin, Jialiang,Ke, Mingji,Cuo, Deji,et al. DBU-Catalyzed Benzannulation towards Stilbene and Biaryl Derivatives from Acyclic Amides with Methyl Coumalate[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2023,27(1).

Qin, Jialiang.,Ke, Mingji.,Cuo, Deji.,Xin, Shangping.,Xue, Yongbo.,...&Huang, Huicai.(2023).DBU-Catalyzed Benzannulation towards Stilbene and Biaryl Derivatives from Acyclic Amides with Methyl Coumalate.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,27(1).

Qin, Jialiang,et al."DBU-Catalyzed Benzannulation towards Stilbene and Biaryl Derivatives from Acyclic Amides with Methyl Coumalate".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 27.1(2023).