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

Kare Nagaraju; Nomula Rajesh; Palakodety Radha Krishna

doi:10.1055/s-0037-1609517

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CC BY ND NC 4.0 · SynOpen 2018; 02(02): 0145-0149
DOI: 10.1055/s-0037-1609517

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

Kare Nagaraju

^aD-211, Discovery Laboratory, Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India

^bAcademy of Scientific and Innovative Research (AcSIR), New Delhi-110025, India eMail: prkgenius@iict.res.in

,

Nomula Rajesh

^aD-211, Discovery Laboratory, Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India

,

Palakodety Radha Krishna*

^aD-211, Discovery Laboratory, Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India

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Abstract

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

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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

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