Synthesis of Spiro[5.5]trienones- and Spiro[4.5]trienones-Fused Selenocyanates via Electrophilic Selenocyanogen Cyclization and Dearomative Spirocyclization

被引：9

作者：

Wang, Jia ^{[1
]}

Lu, Xiao-Xiao ^{[1
]}

Yang, Run-Ping ^{[1
]}

Xiang, Zhi-Hao ^{[1
]}

Zhang, Bing-Bing ^{[1
]}

Chao, Shujun ^{[1
]}

Liu, Lixia ^{[1
]}

Yan, Yunhui ^{[1
]}

Shang, Xuefang ^{[1
]}

机构：

[1] Xinxiang Med Univ, Sch Basic Med Sci, Xinxiang 453003, Henan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 19期

关键词：

INTRAMOLECULAR CYCLIZATION; REGIOSELECTIVE SYNTHESIS; IRON(III) CHLORIDE; DERIVATIVES; IDENTIFICATION; DISELENIDES; SELENIUM; SE;

D O I：

10.1021/acs.joc.2c01594

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical strategy for the synthesis of spiro[5.5]trienones-fused selenocyanates and spiro[4.5]trienones-fused selenocyanates through electrophilic selenocyanogen cyclization and dearomative spirocyclization is reported. This approach was conducted under mild conditions with broad substrate scope and good functional group tolerance. The utility of this procedure is exhibited in the late-stage functionalization of nature product and drug molecules.

引用

页码：13089 / 13101

页数：13

共 44 条

[1] Synthesis of Trifluoromethylselenolated Spiro[5.5]trienones/Spiro[4.5]trienones via Electrophilic Trifluoromethylselenolation Cyclization and Dearomatization
Wang, Jia
Niu, Jia-Qi
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ADVANCED SYNTHESIS & CATALYSIS, 2024,
[2] Synthesis of Difluoromethylated and Phosphorated Spiro[5.5]trienones via Dearomative Spirocyclization of Biaryl Ynones
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ORGANIC LETTERS, 2018, 20 (10) : 2988 - 2992
[3] Electrochemical Synthesis of Spiro[4.5]trienones through Radical-Initiated Dearomative Spirocyclization
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[4] Rapid Access to Sulfenylated Spiro[5.5]trienones via PIFA-promoted Dearomative Spirocyclization of Biaryl Ynones
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[6] Synthesis of polychloromethylated and halogenated spiro[5,5]trienones via dearomative spirocyclization of biaryl ynones
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[10] Electrochemical synthesis of 3-halogenated spiro [4,5]trienones based on dearomative spirocyclization strategy
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