Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York A Convenient Synthesis of 3-(1-Aminoalkyl)quinolin-2(1 H )-one Derivatives Kazuhiro Kobayashi*, Yuhei Fuchimoto, Kazutaka Hayashi, Masaaki Mano, Miyuki Tanmatsu, Osamu Morikawa, Hisatoshi KonishiDepartment of Materials Science, Faculty of Engineering, Tottori University, Koyama-minami, Tottori 680-8552, JapanFax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp; Recommend Article Abstract Buy Article All articles of this category Abstract Treatment of magnesium enolates of 1-methyl-3,4-dihydroquinolin-2(1H)-ones with nitriles, followed by N-acetylation of the resulting vinylogous urea derivatives with acetic anhydride/pyridine and double bond migration with 1,8-diazabicyclo[5.3.0]undec-7-ene, affords 3-[1-(acetylamino)alkyl]-1-methylquinolin-2(1H)-one derivatives in reasonable overall yields. Key words carbanion - lactams - magnesium - nitriles - quinolines Full Text References References 1a DeVita RJ. Walsh TF. Young JR. Jiang J. Ujjainwalla F. Toupence RB. Parikh M. Huang SX. Fair JA. Goulet MT. Wyvratt MJ. Lo J.-L. Ren N. Yudkovitz JB. Yang YT. Cheng K. Cui J. Mount G. Rohrer SP. Schaeffer JM. Rohdes L. Drisko JE. McGowan E. Macintyre DE. Vincent S. Carlin JR. Cameron J. Smith RG. J. Med. Chem. 2001, 44: 917 1b Hewawasam P. Fan W. Knipe J. Moon SL. Boissard CG. Gribkoff VK. Starrett JE. Lodge NJ. Bioorg. Med. Chem. Lett. 2002, 12: 1779 1c Angibaud P. Bourdrez X. Devine A. End DW. Freyne E. Lingy Y. Muller P. Mannens G. Pilatte I. Poncelet V. Skrzat S. Smets G. Dun JV. Remoortere PV. Venet M. Wouters W. Bioorg. Med. Chem. Lett. 2003, 13: 1543 1d Hewawasam P. Fan W. Ding M. Cook D. Goggins GD. Mters RA. Gribkoff VK. Boissard CG. Dworetzky SI. Starrett JE. Lodge NJ. J. Med. Chem. 2003, 46: 2819 1e Jiang J. DeVita RJ. Goulet MT. Wyvratt MJ. Lo J.-L. Ren N. Yudkovitz JB. Cui J. Yang YT. Cheng K. Rohrer SP. Bioorg. Med. Chem. Lett. 2004, 14: 1795 1f Marcaccini S. Pepino R. Pozo MC. Basurto S. García-Valverde M. Torroba T. Tetrahedron Lett. 2004, 45: 3999 1g Hewawasam P. Fan W. Cook DA. Newberry KS. Boissard CG. Gribkoff VK. Starrett JE. Lodge NJ. Bioorg. Med. Chem. Lett. 2004, 14: 4479 1h DeVita RJ. Parikh M. Jiang J. Fair JA. Young JR. Walsh TF. Goulet MT. Lo J.-L. Ren N. Yudkovitz JB. Cui J. Yang YT. Cheng K. Rohrer SP. Wyvratt MJ. Bioorg. Med. Chem. Lett. 2004, 14: 5599 ; and references cited therein See, e.g.: 2a Asherson JL. Young DW. J. Chem. Soc., Chem. Commun. 1977, 916 2b Jha IS. Kanth AK. Singh L. Orient. J. Chem. 1998, 14: 489 ; Chem. Abstr. 1999, 130, 281972h 3a Hiyama T. Kobayashi K. Tetrahedron Lett. 1982, 23: 1597 3b Kobayashi K. Suginome H. Bull. Chem. Soc. Jpn. 1986, 59: 2635 3c Hiyama T. Kobayashi K. Nishide K. Bull. Chem. Soc. Jpn. 1987, 60: 2127 3d Kobayashi K. Kanno Y. Seko S. Suginome H. J. Chem. Soc., Chem. Commun. 1992, 780 4 Kobayashi K. Kitamura T. Nakahashi R. Shimizu A. Morikawa O. Konishi H. Heterocycles 2000, 53: 1021 For other recent reports from our laboratory on the heterocycle synthesis utilizing magnesium enolates, see: 5a Kobayashi K. Takabatake H. Kitamura T. Morikawa O. Konishi H. Bull. Chem. Soc. Jpn. 1997, 70: 1697 5b Kobayashi K. Nakahashi R. Shimizu A. Kitamura T. Morikawa O. Konishi H. J. Chem. Soc., Perkin Trans. 1 1999, 1747 5c Kobayashi K. Matoba T. Irisawa S. Takanohashi A. Tanmatsu M. Morikawa O. Konishi H. Bull. Chem. Soc. Jpn. 2000, 73: 2805 5d Kobayashi K. Nakashima T. Mano M. Morikawa O. Konishi H. Chem. Lett. 2001, 602 5e Kobayashi K. Nakahashi R. Mano M. Morikawa O. Konishi H. Bull. Chem. Soc. Jpn. 2003, 76: 1257 5f Kobayashi K. Honma K. Kondo S. Morikawa O. Konishi H. Heterocycles 2005, 65: 619 ; and references cited therein 6 2,3-Dihydroquinolin-2(1H)-one was commercially available and the others were prepared by the procedure reported in the following paper: Guaruna A. Machetti F. Occhiato EG. Scarpi D. J. Med. Chem. 2000, 43: 3718 7 Morfat A. Carta M. Synthesis 1987, 515 8 Venkov AP. Statkova-Abeghe SM. Tetrahedron 1996, 52: 1451
