Syntheses of 2-Aroyl Benzofurans through Cascade Annulation on Arynes

被引：50
|
作者：
Gouthami, Pashikanti [1 ]
Chavan, Lahu N. [1 ,3 ]
Chegondi, Rambabu [2 ,3 ]
Chandrasekhar, Srivari [1 ,3 ]
机构：
[1] Indian Inst Chem Technol, CSIR, Nat Prod Chem Div, Hyderabad 500007, Andhra Prades, India
[2] Indian Inst Chem Technol, CSIR, Organ & Biomol Chem Div, Hyderabad 500007, Andhra Prades, India
[3] Acad Sci & Innovat Res AcSIR, New Delhi 110025, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 06期
关键词：
ORTHO-QUINONE METHIDE; ORGANIC-SYNTHESIS; STRAIGHTFORWARD SYNTHESIS; BIOLOGICAL EVALUATION; COUPLING REACTION; NATURAL-PRODUCTS; INSERTION; BOND; HETEROCYCLES; DERIVATIVES;
D O I：
10.1021/acs.joc.8b00360
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The highly efficient and expedient route for the syntheses of 2-aroyl benzofurans has been developed via the cascade [2+2] followed by a [4+1] annulation on arynes. The overall transformation proceeded through the formation of ortho-quinone methide by the insertion of transient aryne into N,N-dimethylformamide and subsequent trapping with sulfur ylide. Moreover, this transformation has a broad range of substrate scope with a high functional -group tolerance. This new reaction was successfully utilized in the synthesis of the potent CYP19 aromatase inhibitor and late -stage functionalization on the bioactive complex estrone.
引用
收藏
页码：3325 / 3332
页数：8
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