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CC BY ND NC 4.0 · SynOpen 2018; 02(02): 0145-0149
DOI: 10.1055/s-0037-1609517
DOI: 10.1055/s-0037-1609517
paper
Synthesis of Phthalimides: A New Entry via TBAI-Catalyzed Intramolecular Cyclization of 2-(Hydroxymethyl)benzamides
K. N. and N. R. thank CSIR New Delhi for Research Fellowships. This research work was financially supported by the CSIR, New Delhi (BSC 0116).Further Information
Publication History
Received: 21 March 2018
Accepted after revision: 19 April 2018
Publication Date:
16 May 2018 (online)

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 - oxidationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609517.
- Supporting Information
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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
- 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
- 1d Balzarini EJ. Clercq D. Kaminska B. Orzeszko A. Antiviral Chem. Chemother. 2003; 14: 139
- 1e Franks ME. Macpherson GR. Figg WD. Lancet 2004; 363: 1802
- 1f Luzzio FA. Duveau DY. Lepper ER. Figg WD. J. Org. Chem. 2005; 70: 10117
- 1g Shoji A. Kuwahara M. Ozaki H. Sawai H. J. Am. Chem. Soc. 2007; 129: 1456
- 2 Shinji C. Maeda S. Imai K. Yoshida M. Hashimoto Y. Miyachi H. Bioorg. Med. Chem. 2006; 14: 7625
- 3 Zhang J. Senthilkumar M. Ghosh SC. Hong SH. Angew. Chem. Int. Ed. 2010; 49: 6391
- 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
- 6 Naota T. Murahashi SI. Synlett 1991; 693
- 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
- 8b Yuan Y. Hou W. Negrerie DZ. Zhao K. Du Y. Org. Lett. 2014; 16: 5410
- 8c Aruri H. Singh U. Kumar S. Kushwaha M. Gupta AP. Vishwakarma RA. Singh PP. Org. Lett. 2016; 18: 3638
- 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
- 11 Rohith S. Rao AS. Pralhad JN. Vishal R. Chem. Commun. 2015; 473
- 12 Nammalwar B. Muddala NP. Watts FM. Bunce RA. Tetrahedron 2015; 71: 9101