Synlett, Table of Contents LETTER © Georg Thieme Verlag Stuttgart ˙ New York NaIO4-Mediated Decarboxylative Oxidation of γ-Lactam Carboxylic Acids: A Simple Approach towards N-Aryl Maleimide Derivatives Gopa Barman, Jayanta K. Ray*Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, Indiae-Mail: jkray@chem.iitkgp.ernet.in; e-Mail: rayjayanta@hotmail.com; Recommend Article Abstract Buy Article All articles of this category Abstract A simple methodology has been developed for the synthesis of N-aryl maleimides from N-aryl γ-lactam-2-carboxylic acids by decaboxylative oxidation and dehydrogenation with the oxidant NaIO4/LiBr in refluxing acetonitrile-water solvent. Key words maleimides - decarboxylation - oxidation - γ-lactam 2-carboxylic acids - bromination Full Text References References 1 Walker MA. J. Org. Chem. 1986, 60: 5352 2a Janda KD. Ashley JA. Jones TM. McLeod DA. Schloeder DM. Weinhouse MI. J. Am. Chem. Soc. 1990, 112: 8886 2b Rusiecki VK. Warne SA. Bioorg. Med. Chem. Lett. 1993, 3: 707 3 Shigemitsu Y. Komiya K. Mizuyama N. Tominaga Y. Dyes Pigm. 2007, 72: 271 4 Alizadeh A. Movahedi F. Esmaili AA. Tetrahedron Lett. 2006, 47: 4469 5 Sortino M. Filho VC. Corrêa R. Zacchino S. Bioorg. Med. Chem. 2008, 16: 560 6a Metha NB. Phillips AP. Lui LF. Brooks RE. J. Org. Chem. 1960, 25: 1012 6b Rich DH. Gesellechen PD. Tong A. Cheung A. Buckner CK. J. Med. Chem. 1975, 18: 1004 6c Gill GB. James GD. Oates KV. Pattenden G. J. Chem. Soc., Perkin Trans. 1 1993, 2567 6d Meyers AI. Lefiar BA. Sowin TJ. Westrum LJ. J. Org. Chem. 1989, 54: 4243 6e Miller SA. Chamberlin AR. J. Org. Chem. 1989, 54: 2502 6f Garner P. Ho WB. Grandhee SK. Youngs WJ. Kennedy VO. J. Org. Chem. 1991, 56: 5893 7 Barman G. Roy M. Ray JK. Tetrahedron Lett. 2008, 49: 405 8 Trahanovsky WS. Cramer J. Brixius DW. J. Am. Chem. Soc. 1974, 96: 1077 9 Sayre LM. Jensen FR. J. Org. Chem. 1978, 43: 25 10 Murahashi SI. Imada Y. Ohtake H. J. Org. Chem. 1994, 59: 6170 11 Doyle MP. Whitefleet JL. DeBruyn DJ. Wierenga W. J. Am. Chem. Soc. 1977, 99: 494 12 Cohen T. Song H. Fager JH. Tetrahedron Lett. 1965, 4: 237 13 Shaikh TMA. Emmanuvel L. Sudalai A. J. Org. Chem. 2006, 71: 5043 14 Shaikh TM. Sudalai A. Tetrahedron Lett. 2005, 46: 5587 15 Haldar P. Barman G. Ray JK. Tetrahedron 2007, 63: 3049 16a Barton DHR. Lachera B. Zard SZ. Tetrahedron 1987, 43: 4321 16b Telvekar VN. Chettiar SN. Tetrahedron Lett. 2007, 48: 4529 Supplementary Material Supplementary Material Supporting Information
