Download PDF
Synthesis 2008(16): 2561-2568  
DOI: 10.1055/s-2008-1078601
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Synthesis of 2-Hydroxy-7,8-dihydroquinolin-5(6H)-ones and 7,8-Dihydroquinoline-2,5(1H,6H)-diones from Morita-Baylis-Hillman Adduct Acetates

Weihui Zhong, Fuliang Lin, Ren’er Chen, Weike Su*
College of Pharmaceutical Sciences, Zhejiang University of Technology, Zhejiang Key Laboratory of Pharmaceutical Engineering, Hangzhou 310014, P. R. of China
Fax: +86(571)88320752; e-Mail: suweike@zjut.edu.cn;
Further Information

Publication History

Received 28 February 2008
Publication Date:
17 July 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

A series of 2-hydroxy-7,8-dihydroquinolin-5(6H)-ones and 7,8-dihydroquinoline-2,5(1H,6H)-diones have been synthesized in good to excellent yields from Morita-Baylis-Hillman ­adduct acetates, cyclohexane-1,3-diones and ammonium acetate or primary amines in one pot under solvent-free conditions.

Key words

2-hydroxy-7,8-dihydroquinolin-5(6H)-ones - 7,8-dihydroquinoline-2,5(1H,6H)-diones - Morita-Baylis-Hillman adduct acetates - cyclohexane-1,3-diones - solvent-free conditions

    References

  • 1a Raffaella B. Michele F. Paola F. Luisa M. Quant. Struct.-Act. Relat.  1997,  16:  201 
    Google Scholar
  • 1b El-Sheikh MI. Cook JM. J. Org. Chem.  1980,  45:  2585 
    Google Scholar
  • 2a Carlier PR. Du DM. Han YF. Liu J. Perola E. Williams ID. Pang YP. Angew. Chem. Int. Ed.  2000,  39:  1775 
    Google Scholar
  • 2b Rivikin A. Adams B. Tetrahedron Lett.  2006,  47:  2395 
    Google Scholar
  • 2c Christos AM. Alexandros LZ. Olga IM. J. Org. Chem.  2003,  68:  4567 
    Google Scholar
  • 2d Pita B. Masaguer CF. Raviña E. Tetrahedron Lett.  2002,  43:  7929 
    Google Scholar
  • 2e Lee YR. Kweon HI. Koh WS. Min KR. Kim Y. Lee SH. Synthesis  2001,  1851 
    Google Scholar
  • 3 Anderson WK. Dean DC. Endo T. J. Med. Chem.  1990,  33:  1667 
    CrossrefGoogle Scholar
  • 4 Pita B. Masaguer CF. Raviña E. Tetrahedron Lett.  2000,  41:  9829 
    CrossrefGoogle Scholar
  • 5 Li Q. Mitscher LA. Shen LL. Med. Res. Rev.  2000,  20:  231 
    CrossrefGoogle Scholar
  • 6a Gorobets NY. Yousefi BH. Belaj F. Kappe CO. Tetrahedron  2004,  60:  8633 
    Google Scholar
  • 6b Dorigo P. Gaion RM. Belluco P. Fraccarollo D. Maragno I. Bombierij G. Benetollo F. Mosti L. Orsinil F. J. Med. Chem.  1993,  36:  2475 
    Google Scholar
  • 7 Bar G. Parsons AF. Thomas CB. Tetrahedron Lett.  2000,  41:  7751 
    Google Scholar
  • 8a Morita K. Suzuki Z. Hirose H. Bull. Chem. Soc. Jpn.  1968,  41:  2815 
    Google Scholar
  • 8b Basavaiah D. Rao PD. Hyma RS. Tetrahedron  1996,  52:  8001 
    Google Scholar
  • 8c Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev.  2003,  103:  811 
    Google Scholar
  • 9a Narender P. Gangadasu B. Ravinder M. Srinavas U. Swamy GYSK. Ravikumar K. Rao VJ. Tetrahedron  2006,  62:  954 
    Google Scholar
  • 9b Berthiol F. Doucet H. Santelli M. Tetrahedron  2006,  62:  4372 
    Google Scholar
  • 9c Madapa S. Singh V. Batra S. Tetrahedron  2006,  62:  8740 
    Google Scholar
  • 9d Singh V. Kanojiya S. Batra S. Tetrahedron  2006,  62:  10100 
    Google Scholar
  • 9e Lee CG. Lee KY. Lee S. Kim JN. Tetrahedron  2005,  61:  1493 
    Google Scholar
  • 9f Lee KY. Kim JM. Kim JN. Tetrahedron  2003,  59:  385 
    Google Scholar
  • 9g Basavaiah D. Reddy RM. Kumaragurubaran N. Sharada DS. Tetrahedron  2002,  58:  3693 
    Google Scholar
  • 9h Im YJ. Lee KY. Kim TH. Kim JN. Tetrahedron Lett.  2002,  43:  4675 
    Google Scholar
  • 10a Kantam ML. Kumar KBS. Sreedhar B. J. Org. Chem.  2008,  73:  320 
    Google Scholar
  • 10b He L. Jian TY. Ye S. J. Org. Chem.  2007,  72:  7466 
    Google Scholar
  • 10c Pohamakotr M. Thamapipol S. Tuchinda P. Prabpai S. Kongsaeree P. Rutrakul V. J. Org. Chem.  2007,  72:  5418 
    Google Scholar
  • 10d Park H. Cho CW. Krische MJ. J. Org. Chem.  2006,  71:  7892 
    Google Scholar
  • 10e Singh V. Saxena R. Batra S. J. Org. Chem.  2005,  70:  353 
    Google Scholar
  • 10f Krishna PR. Kannan V. Sharma GVM. J. Org. Chem.  2004,  69:  6467 
    Google Scholar
  • 10g Kabalka GW. Venkataiah B. Dong G. J. Org. Chem.  2004,  69:  5807 
    Google Scholar
  • 10h Alcaide B. Almendros P. Aragoncillo C. Acebes RR. J. Org. Chem.  2004,  69:  826 
    Google Scholar
  • 10i Kinoshita H. Osamura T. Kinoshita S. Iwamura T. Watanabe SI. Kataoka T. Tanabe G. Muraoka O. J. Org. Chem.  2003,  68:  7532 
    Google Scholar
  • 10j Reddy MVR. Rudd MT. Ramachandran PV. J. Org. Chem.  2002,  67:  5382 
    Google Scholar
  • 10k Jauch J. J. Org. Chem.  2001,  66:  609 
    Google Scholar
  • 10l Rafel S. Leahy JW. J. Org. Chem.  1997,  62:  1521 
    Google Scholar
  • 11a Ruda MC. Bergman J. Koehler K. Liu Y. Heterocycl. Commun.  2003,  9:  571 
    Google Scholar
  • 11b Al-Mousawi S. Abdel-Khalik MM. John E. Elnagdi MH. J. Heterocycl. Chem.  2003,  40:  689 
    Google Scholar
  • 11c Carlier PR. Du D. Han Y. Liu J. Pang Y. Bioorg. Med. Chem. Lett.  1999,  9:  2335 
    Google Scholar
  • 11d Singh K. Singh J. Singh H. Tetrahedron  1998,  54:  935 
    Google Scholar
  • 11e Gatta F. Del Giudice MR. Pomponi M. Marta M. Heterocycles  1992,  34:  991 
    Google Scholar
  • 11f Pettit GR. Fleming WC. Paull KD. J. Org. Chem.  1968,  33:  1089 
    Google Scholar
  • 11g Fossa P. Menozzi G. Dorigo P. Floreani M. Mosti L. Bioorg. Med. Chem.  2003,  11:  4749 
    Google Scholar
  • 11h Oehldrich J. Cook JM. J. Org. Chem.  1977,  42:  889 
    Google Scholar
  • 11i Grizik SI. Solov’eva NP. Granik VG. Yuzhakov SD. Dolgun OV. Dugin SF. Medvedev OS. Mashkovskii MD. Pharm. Chem. J.  1995,  29:  618 
    Google Scholar
  • 11j Abu-Shanab FA. Redhouse AD. Thompson JR. Wakefield BJ. Synthesis  1995,  557 
    Google Scholar
  • 12a Fernández M. Cuesta E. Avendaño C. Heterocycles  1994,  38:  2615 
    Google Scholar
  • 12b Kočevar M. Polanc S. Tišler M. Verček B. Heterocycles  1990,  30:  227 
    Google Scholar
  • 12c Fukatsu H. Kato Y. Murase S. Nakagawa S. Heterocycles  1989,  29:  1517 
    Google Scholar
  • 12d Chang J.-C. El-Sheikh MI. Cook JM. Heterocycles  1979,  12:  903 
    Google Scholar
  • 12e El-Sheikh MI. Chang J.-C. Cook JM. Heterocycles  1978,  9:  1561 
    Google Scholar
  • 13 Gowrisankar S. Na JE. Lee MJ. Kim JN. Bull. Korean Chem. Soc.  2005,  26:  319 
    CrossrefGoogle Scholar
  • 14 Zhong W. Zhao Y. Su W. Tetrahedron  2008,  64:  5491 
    CrossrefGoogle Scholar