An efficient synthesis of a class of novel N-alkyl-N-aryl-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-3- quinolinecarbothioamides

Journal of Heterocyclic Chemistry

Volumn 39, Issue 4, 2002, Pages 799-804

  Spears, Glen W ^a   Tsuji, Kiyoshi ^a   Tojo, Takashi ^a   Nishimura, Hiroaki ^a   Ogino, Takashi ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXY 1 METHYL 2 OXO 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; 4 HYDROXY N,1 DIMETHYL 2 OXO N PHENYL 6 (1H PYRROL 1 YL) 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; 4 HYDROXY N,1 DIMETHYL 6 (METHYLTHIO) 2 OXO N PHENYL 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; 6 CHLORO 4 HYDROXY N (4 METHOXYPHENYL) N,1 DIMETHYL 2 OXO 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; 6 CHLORO 4 HYDROXY N,1 DIMETHYL 2 OXO N (2 THIENYL) 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; 6 CHLORO 4 HYDROXY N,1 DIMETHYL 2 OXO N PHENYL 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; 6 CHLORO 4 HYDROXY N,1 DIMETHYL 2 OXO N [3 (TRIFLUOROMETHYL)PHENYL] 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; 6 CHLORO N (4 CHLOROPHENYL) 4 HYDROXY N 1,8 TRIMETHYL 2 OXO 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; 6 HYDROXY 6 METHOXY N,1 DIMETHYL 2 OXO N [3 (TRIFLUOROMETHYL)PHENYL] 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; ACID ANHYDRIDE; FR 142107; IMMUNOMODULATING AGENT; N (4 CHLOROPHENYL) 4 HYDROXY 6 METHOXY N,1 DIMETHYL 2 OXO 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; N (4 CHLOROPHENYL) 4 HYDROXY N,1 DIMETHYL 2 OXO 6 (TRIFLUOROMETHOXY) 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; N TERT BUTYL 6 CHLORO 4 HYDROXY 1 METHYL 2 OXO N PHENYL 1,2 DIHYDRO 3 QUINOLINECARBOTHIOAMIDE; QUINOLINE DERIVATIVE; ROQUINIMEX; THIOAMIDE; UNCLASSIFIED DRUG;

ACYLATION; ALKYLATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0036666741     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570390427     Document Type: Article

References (20)

1. C. Robinson and J. Castaner, Drugs of the Future, 20, 19 (1995).
2. M. Matsuo, K. Tsuji, G. W. Spears, T. Ogino, H. Nishimura, and T. Tojo, PCT Int. Appl. WO95-24395 (1995). Chem. Abstr., 124, 117102e (1995).
3. For similar reactions of activated methylene compounds with isatoic anhydrides see the following: G. M. Coppola and G. E. Hardtmann, J. Heterocyclic Chem., 16, 1605 (1979); G. M. Coppola, G. E. Hardtmann, and O. R. Pfister, J. Org. Chem., 41, 825 (1976); S. R. Khan, A. Mhaka, R. Pili, and J. T. Isaacs, Bioorg. Med. Chem. Lett., 11, 451 (2001); G. M. Coppola, R. E. Damon, G. E. Hardtmann, Synthesis, 391 (1981); L. Ismaili, B. Refouvelet, and J. F. Robert, J. Heterocyclic Chem., 36, 719 (1999).
4. For similar reactions of activated methylene compounds with isatoic anhydrides see the following: G. M. Coppola and G. E. Hardtmann, J. Heterocyclic Chem., 16, 1605 (1979); G. M. Coppola, G. E. Hardtmann, and O. R. Pfister, J. Org. Chem., 41, 825 (1976); S. R. Khan, A. Mhaka, R. Pili, and J. T. Isaacs, Bioorg. Med. Chem. Lett., 11, 451 (2001); G. M. Coppola, R. E. Damon, G. E. Hardtmann, Synthesis, 391 (1981); L. Ismaili, B. Refouvelet, and J. F. Robert, J. Heterocyclic Chem., 36, 719 (1999).
5. For similar reactions of activated methylene compounds with isatoic anhydrides see the following: G. M. Coppola and G. E. Hardtmann, J. Heterocyclic Chem., 16, 1605 (1979); G. M. Coppola, G. E. Hardtmann, and O. R. Pfister, J. Org. Chem., 41, 825 (1976); S. R. Khan, A. Mhaka, R. Pili, and J. T. Isaacs, Bioorg. Med. Chem. Lett., 11, 451 (2001); G. M. Coppola, R. E. Damon, G. E. Hardtmann, Synthesis, 391 (1981); L. Ismaili, B. Refouvelet, and J. F. Robert, J. Heterocyclic Chem., 36, 719 (1999).
6. For similar reactions of activated methylene compounds with isatoic anhydrides see the following: G. M. Coppola and G. E. Hardtmann, J. Heterocyclic Chem., 16, 1605 (1979); G. M. Coppola, G. E. Hardtmann, and O. R. Pfister, J. Org. Chem., 41, 825 (1976); S. R. Khan, A. Mhaka, R. Pili, and J. T. Isaacs, Bioorg. Med. Chem. Lett., 11, 451 (2001); G. M. Coppola, R. E. Damon, G. E. Hardtmann, Synthesis, 391 (1981); L. Ismaili, B. Refouvelet, and J. F. Robert, J. Heterocyclic Chem., 36, 719 (1999).
7. For similar reactions of activated methylene compounds with isatoic anhydrides see the following: G. M. Coppola and G. E. Hardtmann, J. Heterocyclic Chem., 16, 1605 (1979); G. M. Coppola, G. E. Hardtmann, and O. R. Pfister, J. Org. Chem., 41, 825 (1976); S. R. Khan, A. Mhaka, R. Pili, and J. T. Isaacs, Bioorg. Med. Chem. Lett., 11, 451 (2001); G. M. Coppola, R. E. Damon, G. E. Hardtmann, Synthesis, 391 (1981); L. Ismaili, B. Refouvelet, and J. F. Robert, J. Heterocyclic Chem., 36, 719 (1999).
8. G. Benz, Comprehensive Organic Synthesis, Vol. 6, B. M. Trost, Editor-in-Chief, Pergamon Press, Inc., New York, 1991, p 381.
9. For related examples of Dieckmann reactions see: B. R. Davis and P. J. Garratt, Comprehensive Organic Synthesis, Vol. 2, B. M. Trost, Editor-in-Chief, Pergamon Press, Inc., New York, 1991, p 806; W. Chai and W. V. Murray, Tetrahedron Lett., 40, 7185 (1999); M. J. Ashton, S. J. Hills, C. G. Newton, J. B. Taylor, S. C. D. Todou, Heterocycles, 28, 1015 (1989); K. Akiba, M. Nakatani, M. Wada, and Y. Yamamoto, J. Org. Chem., 50, 63 (1985); I. V. Micovic, G. M. Roglic, M. D. Ivanovic, L. Dosen-Micovic, V. D. Kiricojevic, and J. B. Popovic, J. Chem. Soc., Perkin Trans. 1, 2041 (1996).
10. For related examples of Dieckmann reactions see: B. R. Davis and P. J. Garratt, Comprehensive Organic Synthesis, Vol. 2, B. M. Trost, Editor-in-Chief, Pergamon Press, Inc., New York, 1991, p 806; W. Chai and W. V. Murray, Tetrahedron Lett., 40, 7185 (1999); M. J. Ashton, S. J. Hills, C. G. Newton, J. B. Taylor, S. C. D. Todou, Heterocycles, 28, 1015 (1989); K. Akiba, M. Nakatani, M. Wada, and Y. Yamamoto, J. Org. Chem., 50, 63 (1985); I. V. Micovic, G. M. Roglic, M. D. Ivanovic, L. Dosen-Micovic, V. D. Kiricojevic, and J. B. Popovic, J. Chem. Soc., Perkin Trans. 1, 2041 (1996).
11. For related examples of Dieckmann reactions see: B. R. Davis and P. J. Garratt, Comprehensive Organic Synthesis, Vol. 2, B. M. Trost, Editor-in-Chief, Pergamon Press, Inc., New York, 1991, p 806; W. Chai and W. V. Murray, Tetrahedron Lett., 40, 7185 (1999); M. J. Ashton, S. J. Hills, C. G. Newton, J. B. Taylor, S. C. D. Todou, Heterocycles, 28, 1015 (1989); K. Akiba, M. Nakatani, M. Wada, and Y. Yamamoto, J. Org. Chem., 50, 63 (1985); I. V. Micovic, G. M. Roglic, M. D. Ivanovic, L. Dosen-Micovic, V. D. Kiricojevic, and J. B. Popovic, J. Chem. Soc., Perkin Trans. 1, 2041 (1996).
12. For related examples of Dieckmann reactions see: B. R. Davis and P. J. Garratt, Comprehensive Organic Synthesis, Vol. 2, B. M. Trost, Editor-in-Chief, Pergamon Press, Inc., New York, 1991, p 806; W. Chai and W. V. Murray, Tetrahedron Lett., 40, 7185 (1999); M. J. Ashton, S. J. Hills, C. G. Newton, J. B. Taylor, S. C. D. Todou, Heterocycles, 28, 1015 (1989); K. Akiba, M. Nakatani, M. Wada, and Y. Yamamoto, J. Org. Chem., 50, 63 (1985); I. V. Micovic, G. M. Roglic, M. D. Ivanovic, L. Dosen-Micovic, V. D. Kiricojevic, and J. B. Popovic, J. Chem. Soc., Perkin Trans. 1, 2041 (1996).
13. For related examples of Dieckmann reactions see: B. R. Davis and P. J. Garratt, Comprehensive Organic Synthesis, Vol. 2, B. M. Trost, Editor-in-Chief, Pergamon Press, Inc., New York, 1991, p 806; W. Chai and W. V. Murray, Tetrahedron Lett., 40, 7185 (1999); M. J. Ashton, S. J. Hills, C. G. Newton, J. B. Taylor, S. C. D. Todou, Heterocycles, 28, 1015 (1989); K. Akiba, M. Nakatani, M. Wada, and Y. Yamamoto, J. Org. Chem., 50, 63 (1985); I. V. Micovic, G. M. Roglic, M. D. Ivanovic, L. Dosen-Micovic, V. D. Kiricojevic, and J. B. Popovic, J. Chem. Soc., Perkin Trans. 1, 2041 (1996).
14. M. Matsuo, K. Tsuji, K. Nakamura and G. W. Spears, PCT Int. Appl. WO92-18483 (1992); Chem. Abstr., 118, 212903b (1993).
15. K. Tsuji, G. W. Spears, K. Nakamura, T. Tojo, N. Seki, A. Sugiyama and M. Matsuo, Bioorg. Med. Chem. Lett., 12, 85 (2002).
16. G. W. Spears, K. Tsuji, T. Tojo, H. Nishimura and T. Ogino, Synth. Commun., 30, 565 (2000).
17. T. Mukaiyama, Angew. Chem. Int. Ed., 18, 707 (1979).
18. H. Ogura, T. Kobayashi, K. Shimizu, K. Kawabe and K. Takeda, Tetrahedron Lett., 20, 4745 (1979).
19. J. Dudash, Jr., J. Jiang, S. C. Mayer and M. M. Joullie, Synth. Commun., 23, 349 (1993); J. R. Vaughan, Jr. and R. L. Osato, J. Am. Chem. Soc., 74, 676 (1952).
20. J. Dudash, Jr., J. Jiang, S. C. Mayer and M. M. Joullie, Synth. Commun., 23, 349 (1993); J. R. Vaughan, Jr. and R. L. Osato, J. Am. Chem. Soc., 74, 676 (1952).