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

页码：3325 / 3332

页数：8

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