Bismuth(III)-Catalyzed 1,8-Addition/Cyclization/Rearrangement of Propargylic para-Quinone Methides with 2-Vinylphenol: Synthesis of Indeno[2,1-c]chromenes

被引：5

作者：

Zhang, Xiang-Zhi ^{[1
]}

Zhu, Zhi-Qiang ^{[1
]}

Wu, Teng-Fei ^{[1
]}

Pan, Han-Peng ^{[1
]}

Peng, Jin-Bao ^{[1
]}

Ma, Ai-Jun ^{[1
]}

机构：

[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2023年

关键词：

CAESALPINIA-SAPPAN; FORMAL SYNTHESIS; BRAZILIN; (+/-)-BRAZILIN; 1,8-ADDITION; CONSTRUCTION; CYCLIZATION; APOPTOSIS;

D O I：

10.1021/acs.orglett.3c00179

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The unique reactivity of in situ generated propargylic para-quinone methides as a new type of five-carbon synthon has been discovered by a novel bismuth(III)-catalyzed tandem annulation reaction. This 1,8-addition/cyclization/rearrangement cyclization cascade reaction is characterized by unusual structural reconstruction of 2-vinylphenol, involving cleavage of the C1 '=C2 ' bond and formation of four new bonds. This method provides a convenient and mild approach to generate synthetically important functionalized indeno[2,1-c]chromenes. The mechanism of the reaction is proposed from several control experiments.

引用

页码：1299 / 1304

页数：6

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