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Synthesis 2018; 50(15): 2968-2973
DOI: 10.1055/s-0037-1610039
special topic
© Georg Thieme Verlag Stuttgart · New York

Mn(OAc)3-Mediated Regioselective Radical Alkoxycarbonylation of Indoles, Pyrimidinones, and Pyridinones

Cheng-Kun Li
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, Jiangsu 215123, P. R. of China   Email: jpzou@suda.edu.cn
,
Dong-Liang Zhang
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, Jiangsu 215123, P. R. of China   Email: jpzou@suda.edu.cn
,
Ogundipe Olukayode Olamiji
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, Jiangsu 215123, P. R. of China   Email: jpzou@suda.edu.cn
,
Pei-Zhi Zhang
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, Jiangsu 215123, P. R. of China   Email: jpzou@suda.edu.cn
,
Adedamola Shoberu
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, Jiangsu 215123, P. R. of China   Email: jpzou@suda.edu.cn
,
Jian-Ping Zou*
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, Jiangsu 215123, P. R. of China   Email: jpzou@suda.edu.cn
,
Wei Zhang  *
b   Department of Chemistry, University of Massachusetts Boston, MA 02125, USA   Email: wei2.zhang@umb.edu
› Author AffiliationsJ.-P. Z appreciates the generous financial support from National Natural Science Foundation of China (No. 21172163, 21472133), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), Key Laboratory of Organic Synthesis of Jiangsu Province (KJS1749) & State, and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials.
Further Information

Publication History

Received: 28 February 2018

Accepted after revision: 30 April 2018

Publication Date:
04 July 2018 (online)

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Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

Mn(OAc)3-mediated alkoxycarbonylation of indoles, pyrimidinones, and pyridinones with alkyl carbazates is reported. The reactions proceed through a radical process to afford regioselectively 3-carboxylated indoles, 5-carboxylated pyrimidinones, and 3-carboxylated pyridin­ones in moderate to good yields under mild reaction conditions.

Key words

radical - alkoxycarbonylation - indoles - pyrimidinones - pyri­dinones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610039.
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