PDF herunterladen
CC BY-ND-NC 4.0 · SynOpen 2018; 02(02): 0145-0149
DOI: 10.1055/s-0037-1609517
paper
Copyright with the author

Synthesis of Phthalimides: A New Entry via TBAI-Catalyzed Intramolecular Cyclization of 2-(Hydroxymethyl)benzamides

Kare Nagaraju
a   D-211, Discovery Laboratory, Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India
b   Academy of Scientific and Innovative Research (AcSIR), New Delhi-110025, India   eMail: prkgenius@iict.res.in
,
Nomula Rajesh
a   D-211, Discovery Laboratory, Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India
,
Palakodety Radha Krishna*
a   D-211, Discovery Laboratory, Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India
› InstitutsangabenK. N. and N. R. thank CSIR New Delhi for Research Fellowships. This research work was financially supported by the CSIR, New Delhi (BSC 0116).
Weitere Informationen

Publikationsverlauf

Received: 21. März 2018

Accepted after revision: 19. April 2018

Publikationsdatum:
16. Mai 2018 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik


Communication No. IICT/Pubs./2018/080

Abstract

Herein we report an unprecedented metal-free TBAI/TBHP mediated C–N bond formation via intramolecular cyclization of 2-(hydroxymethyl)benzamides to furnish N-substituted phthalimides in excellent yields.

Keywords

phthalimide - intramolecular cyclization - transition-metal free - C–N bond formation - oxidation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609517.
  • Supporting Information
 

  • References

    • 1a Matsumoto K. Nagashima K. Kamigauchi T. Kawamura Y. Yasuda Y. Ishii K. Uotani N. Sato T. Nakai H. Terui Y. Kikuchi J. Ikenisi Y. Yoshida T. Kato T. Itazaki H. J. Antibiot. 1995; 4: 439
    • 1b Miyachi H. Azuma A. Ogasawara A. Uchimura E. Watanabe N. Kobayashi Y. Kato F. Kato M. Hashimoto Y. J. Med. Chem. 1997; 40: 2858
      CrossrefPubMed
    • 1c Figg WD. Raje S. Bauer KS. Tompkins A. Venzon D. Bergan R. Chen A. Hamilton M. Pluda J. Reed E. J. Pharm. Sci. 1999; 88: 121
      CrossrefPubMed
    • 1d Balzarini EJ. Clercq D. Kaminska B. Orzeszko A. Antiviral Chem. Chemother. 2003; 14: 139
      CrossrefPubMed
    • 1e Franks ME. Macpherson GR. Figg WD. Lancet 2004; 363: 1802
      CrossrefPubMed
    • 1f Luzzio FA. Duveau DY. Lepper ER. Figg WD. J. Org. Chem. 2005; 70: 10117
      CrossrefPubMed
    • 1g Shoji A. Kuwahara M. Ozaki H. Sawai H. J. Am. Chem. Soc. 2007; 129: 1456
      CrossrefPubMed
  • 2 Shinji C. Maeda S. Imai K. Yoshida M. Hashimoto Y. Miyachi H. Bioorg. Med. Chem. 2006; 14: 7625
    CrossrefPubMed
  • 3 Zhang J. Senthilkumar M. Ghosh SC. Hong SH. Angew. Chem. Int. Ed. 2010; 49: 6391
    CrossrefPubMed
  • 4 Reddy PY. Kondo S. Toru T. Ueno Y. J. Med. Chem. 1997; 62: 2652
  • 5 Ali MA. Moromi SK. Touchy AS. Shimizu KI. ChemCatChem 2016; 8: 891
    Crossref
  • 6 Naota T. Murahashi SI. Synlett 1991; 693
    Artikel in Thieme Connect
  • 7 Nammalwar B. Muddala NP. Watts FM. Bunce RA. Tetrahedron 2015; 9101
    • 8a Hall A. Billinton A. Bristow AK. Brown SH. Chowdhury A. Cutler L. Giblin MP. G. Hayhow TG. Kilford IR. Naylor A. Passingham B. Rawlings DA. Bioorg. Med. Chem. Lett. 2008; 18: 4027
      CrossrefPubMed
    • 8b Yuan Y. Hou W. Negrerie DZ. Zhao K. Du Y. Org. Lett. 2014; 16: 5410
      CrossrefPubMed
    • 8c Aruri H. Singh U. Kumar S. Kushwaha M. Gupta AP. Vishwakarma RA. Singh PP. Org. Lett. 2016; 18: 3638
      CrossrefPubMed
  • 9 Jin Y. Fu H. Yin Y. Jiang Y. Zhaoa Y. Synlett 2007; 901
  • 10 Yuan Y. Hou W. Negrerie DZ. Zhao K. Du Y. Org. Lett. 2014; 16: 5410
    CrossrefPubMed
  • 11 Rohith S. Rao AS. Pralhad JN. Vishal R. Chem. Commun. 2015; 473
    PubMed
  • 12 Nammalwar B. Muddala NP. Watts FM. Bunce RA. Tetrahedron 2015; 71: 9101
    Crossref