Download PDF
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)

    Permissions and Reprints All articles of this category


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.
  • Supporting Information
 

  • References


      • For selected reviews on alkoxycarbonylation of alkenes, alkynes, and allenes, see:
    • 1a Godard C. Muñoz BK. Ruiz A. Claver C. Dalton Trans. 2008; 853
      PubMed
    • 1b Brennführer A. Neumann H. Beller M. ChemCatChem 2009; 1: 28
      Crossref
    • 1c Kalck P. Urrutigoïty M. Inorg. Chim. Acta 2015; 431: 110
      Crossref
    • 1d Liu B. Hu F. Shi B.-F. ACS Catal. 2015; 5: 1863
      Crossref
    • 2a Taniguchi T. Sugiura Y. Zaimoku H. Ishibashi H. Angew. Chem. Int. Ed. 2010; 49: 10154
      CrossrefPubMed
    • 2b Zong Z.-Z. Lu S.-L. Wang W.-X. Li Z.-P. Tetrahedron Lett. 2015; 56: 6719
      Crossref
    • 2c Su Y.-H. Wu Z. Tian S.-K. Chem. Commun. 2013; 49: 6528
      CrossrefPubMed
    • 2d Ding R. Zhang Q.-C. Xu Y.-H. Loh T.-P. Chem. Commun. 2014; 50: 11661
      CrossrefPubMed
    • 2e Wang G. Wang S. Wang J. Chen S.-Y. Yu X.-Q. Tetrahedron 2014; 70: 3466
      Crossref
    • 2f Xu X. Tang Y. Li X. Hong G. Fang M. Du X. J. Org. Chem. 2014; 79: 446
      CrossrefPubMed
    • 2g Tang Y. Zhang M. Li X. Xu X. Du X. Chin. J. Org. Chem. 2015; 35: 875
      Crossref
    • 2h Li X. Fang X. Zhuang S. Liu P. Sun P. Org. Lett. 2017; 19: 3580
      CrossrefPubMed
    • 3a Wang G. Chen S.-Y. Yu X.-Q. Tetrahedron Lett. 2014; 55: 5338
      Crossref
    • 3b Xiao T.-B. Li L.-Y. Lin G.-L. Wang Q.-L. Zhang P. Mao Z.-W. Zhou L. Green Chem. 2014; 16: 2418
      Crossref
    • 3c Pan C.-D. Han J. Zhang H.-L. Zhu C.-J. J. Org. Chem. 2014; 79: 5374
      CrossrefPubMed
    • 3d Li X.-Q. Fang M.-W. Hu P.-Z. Hong G. Tang Y.-C. Xu X.-S. Adv. Synth. Catal. 2014; 356: 2103
      Crossref
  • 4 Gao Y. Lu W. Liu P. Sun P. J. Org. Chem. 2016; 81: 2482
    CrossrefPubMed
    • 5a Sun WB. Ji YF. Pan XQ. Zhou SF. Zou JP. Zhang W. Asekun O. Synthesis 2013; 45: 1529
      Article in Thieme Connect
    • 5b Sun WB. Xue JF. Zhang GY. Zeng RS. An LT. Zhang PZ. Zou JP. Adv. Synth. Catal. 2016; 358: 1753
      Crossref
    • 5c Zhang L. Zhang PZ. Xue JF. Sun WB. Zou JP. Acta Chim. Sinica 2016; 74: 811
      Crossref
    • 6a Nemoto K. Tanaka S. Konno M. Onozawa S. Chiba M. Tanaka Y. Sasaki Y. Okubo R. Hattori T. Tetrahedron 2016; 72: 734
      Crossref
    • 6b Ramesh S. Arunachalam PN. Lalitha A. RSC Adv. 2013; 3: 8666
      Crossref