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：4
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
收藏
页码：1299 / 1304
页数：6
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