Synthesis of Seleno-Dibenzocycloheptenones/Spiro[5.5]Trienones by Radical Cyclization of Biaryl Ynones

被引：28

作者：

Goulart, Helen A. ^{[1
]}

Bartz, Ricardo H. ^{[1
]}

Peglow, Thiago J. ^{[1
]}

Barcellos, Angelita M. ^{[1
]}

Cervo, Rodrigo ^{[2
]}

Cargnelutti, Roberta ^{[2
]}

Jacob, Raquel G. ^{[1
]}

Lenardao, Eder J. ^{[1
]}

Perin, Gelson ^{[1
]}

机构：

[1] Univ Fed Pelotas UFPel, Lab Sintese Organ Limpa LASOL, CCQFA, BR-35496010 Pelotas, RS, Brazil

[2] Univ Fed Santa Maria UFSM, Dept Quim, CCNE, BR-97105900 Santa Maria, RS, Brazil

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 06期

关键词：

INTRAMOLECULAR NICHOLAS REACTIONS; ANTITUMOR AGENTS; ORGANOSELENIUM CHEMISTRY; ANTITUBULIN ACTIVITY; SELENIUM; COLCHICINE; SESQUITERPENE; EFFICIENT; ANALOGS; ACCESS;

D O I：

10.1021/acs.joc.1c03112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein an alternative method for the synthesis of seleno-dibenzocycloheptenones and seleno-spiro[5.5]-trienones through the radical cyclization of biaryl ynones in the presence of diorganyl diselenides, using Oxone as a green oxidizing agent. The reactions were conducted using acetonitrile as the solvent in a sealed tube at 100 degrees C. The protocol is operationally simple and scalable, exhibits high regioselectivity, and allows the synthesis of 24 dibenzocycloheptenones/spiro[5.5]trienones in yields of up to 99%, 17 of which are unpublished compounds. Additionally, synthetic transformations of the prepared compounds, such as oxidation and reduction reactions, are demonstrated.

引用

页码：4273 / 4283

页数：11

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