Organometallic reagent-mediated one-pot synthesis of 3,5,6-trisubstituted naphthostyrils

Tetrahedron Letters

Volumn 44, Issue 20, 2003, Pages 3901-3904

  Liu, Jin Jun ^a   Konzelmann, Fred ^a   Luk, Kin Chun ^a  

^a HOFFMANN LA ROCHE INC   (United States)

Author keywords

C C bond formation; Intramolecular cyclization; Organometallic reagents; Trisubstituted naphthostyril

Indexed keywords

BETA IODOVINYLKETONE; KETONE DERIVATIVE; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; INFRARED SPECTROSCOPY; MICHAEL ADDITION; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037433858     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00826-8     Document Type: Article

References (47)

1. Liu J.J., Konzelmann F., Luk K.C. Tetrahedron Lett. 44:2003;2545-2548 Chen, Y.; Dermatakis, A.; Konzelmann, F. M.; Liu, J.-J.; Luk, K.-C. WO 02/059109 2002.
2. Liu J.J., Konzelmann F., Luk K.C. Tetrahedron Lett. 44:2003;2545-2548 Chen, Y.; Dermatakis, A.; Konzelmann, F. M.; Liu, J.-J.; Luk, K.-C. WO 02/059109 2002.
3. For review articles on CDKs inhibitors, see: (a) Steinman, R. A. Oncogene 2002, 21, 3403-3413; (b) Kato, J.; Tomoda, K.; Arata, Y.; Tanaka, T.; Yoneda-Kato, N. Tumor-Suppressing Viruses, Genes, and Drugs 2002, 21, 123-143; (c) Morgan D. Nature 1995, 374, 131-134 and references cited therein. For a recent example, see: Kim, K. S.; Kimball, S. D.; Misra, R. N.; Rawlins, D. B.; Hunt, J. T.; Xiao, H.-Y.; Lu, S.; Qian, L.; Han, W.-C.; Shan, W.; Mitt, T.; Cai, Z.-W.; Poss, M. A.; Zhu, H.; Sack, J. S.; Tokarski, J. S.; Chang, C. Y.; Pavletich, N.; Kamath, A.; Humphreys, W. G.; Marathe, P.; Bursuker, I.; Kellar, K. A.; Roongta, U.; Batorsky, R.; Mulheron, J. G.; Bol, D.; Fairchild, C. R.; Lee, F. Y.; Webster, K. R. J. Med. Chem. 2002, 45, 3905-3927.
4. For review articles on CDKs inhibitors, see: (a) Steinman, R. A. Oncogene 2002, 21, 3403-3413; (b) Kato, J.; Tomoda, K.; Arata, Y.; Tanaka, T.; Yoneda-Kato, N. Tumor-Suppressing Viruses, Genes, and Drugs 2002, 21, 123-143; (c) Morgan D. Nature 1995, 374, 131-134 and references cited therein. For a recent example, see: Kim, K. S.; Kimball, S. D.; Misra, R. N.; Rawlins, D. B.; Hunt, J. T.; Xiao, H.-Y.; Lu, S.; Qian, L.; Han, W.-C.; Shan, W.; Mitt, T.; Cai, Z.-W.; Poss, M. A.; Zhu, H.; Sack, J. S.; Tokarski, J. S.; Chang, C. Y.; Pavletich, N.; Kamath, A.; Humphreys, W. G.; Marathe, P.; Bursuker, I.; Kellar, K. A.; Roongta, U.; Batorsky, R.; Mulheron, J. G.; Bol, D.; Fairchild, C. R.; Lee, F. Y.; Webster, K. R. J. Med. Chem. 2002, 45, 3905-3927.
5. For review articles on CDKs inhibitors, see: (a) Steinman, R. A. Oncogene 2002, 21, 3403-3413; (b) Kato, J.; Tomoda, K.; Arata, Y.; Tanaka, T.; Yoneda-Kato, N. Tumor-Suppressing Viruses, Genes, and Drugs 2002, 21, 123-143; (c) Morgan D. Nature 1995, 374, 131-134 and references cited therein. For a recent example, see: Kim, K. S.; Kimball, S. D.; Misra, R. N.; Rawlins, D. B.; Hunt, J. T.; Xiao, H.-Y.; Lu, S.; Qian, L.; Han, W.-C.; Shan, W.; Mitt, T.; Cai, Z.-W.; Poss, M. A.; Zhu, H.; Sack, J. S.; Tokarski, J. S.; Chang, C. Y.; Pavletich, N.; Kamath, A.; Humphreys, W. G.; Marathe, P.; Bursuker, I.; Kellar, K. A.; Roongta, U.; Batorsky, R.; Mulheron, J. G.; Bol, D.; Fairchild, C. R.; Lee, F. Y.; Webster, K. R. J. Med. Chem. 2002, 45, 3905-3927.
6. For review articles on CDKs inhibitors, see: (a) Steinman, R. A. Oncogene 2002, 21, 3403-3413; (b) Kato, J.; Tomoda, K.; Arata, Y.; Tanaka, T.; Yoneda-Kato, N. Tumor-Suppressing Viruses, Genes, and Drugs 2002, 21, 123-143; (c) Morgan D. Nature 1995, 374, 131-134 and references cited therein. For a recent example, see: Kim, K. S.; Kimball, S. D.; Misra, R. N.; Rawlins, D. B.; Hunt, J. T.; Xiao, H.-Y.; Lu, S.; Qian, L.; Han, W.-C.; Shan, W.; Mitt, T.; Cai, Z.-W.; Poss, M. A.; Zhu, H.; Sack, J. S.; Tokarski, J. S.; Chang, C. Y.; Pavletich, N.; Kamath, A.; Humphreys, W. G.; Marathe, P.; Bursuker, I.; Kellar, K. A.; Roongta, U.; Batorsky, R.; Mulheron, J. G.; Bol, D.; Fairchild, C. R.; Lee, F. Y.; Webster, K. R. J. Med. Chem. 2002, 45, 3905-3927.
7. Lolli M.L., Lazzarato L., Di Stilo A., Fruttero R., Gasco A. J. Organomet. Chem. 650:2002;77-83.
8. Wang Z.Y., Cui J.L., Du B.S., Chen Q.H. Chinese Chem. Lett. 12:2001;293-296.
9. Kao K.-H., Sheu R.-S., Chen Y.-S., Lin W.-W., Liu J.-T., Yao C.-F. J. Chem. Soc., Perkin Trans. 1. 1999;2383-2390.
10. Kozlowski, J. A. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.4, pp. 169-198.
11. Krause N. Angew. Chem., Int. Ed. Engl. 36:1997;186.
12. Yamazaki T., Shinohara N., Kitazume T., Sato S. J. Fluor. Chem. 97:1999;91-96.
13. Lutz C., Jones P., Knochel P. Synthesis. 2:1999;312-316.
14. Back T.G., Bethell R.J., Parvez M., Wehrli D. J. Org. Chem. 63:1998;7908-7919.
15. Lipshutz B.H., Wood M.R., Tirado R. J. Am. Chem. Soc. 117:1995;6126-6127.
16. Tamaru Y., Tanigawa H., Yamamoto T., Yoshida Z. Angew. Chem. 101:1989;358-360.
17. Negishi E.-I. Organozinc Reagents. 1999;213-243.
18. Feringa B.L. Acc. Chem. Res. 33:2000;346-353.
19. Sibi M.P., Manyem S. Tetrahedron. 56:2000;8033-8061.
20. Kabbara J., Flemming S., Nickisch K., Neh H., Westermann J. Tetrahedron. 51:1995;743-754.
21. Kamimura A., Sasatani H., Hashimoto T., Kawai T., Hori K., Ono N. J. Org. Chem. 55:1990;2437-2442.
22. Lopp M., Parve O., Lille U. Eesti NSV Tead. Akad. Toim., Keem. 29:1980;185-190.
23. Lopp M., Lille U. Eesti NSV Tead. Akad. Toim., Keem. 28:1979;103-107.
24. Piers E., Cheng K.F., Nagakura I. Can. J. Chem. 60:1982;1256-1263.
25. Wender P.A., White A.W. J. Am. Chem. Soc. 110:1988;2218-2223.
26. Majid T.N., Yeh M.C.P., Knochel P. Tetrahedron Lett. 30:1989;5069-5072.
27. Bronk B.S., Lippard S.J., Danheiser R.L. Organometallics. 12:1993;3340-3349.
28. Luo F.-T., Hsieh L.-C., Fwu S.-L., Hwang W.-S. J. Chinese Chem. Soc. 41:1994;605-607.
29. Dieter R.K., Topping C.M., Chandupatla K.R., Lu K. J. Am. Chem. Soc. 123:2001;5132-5133.
30. Lopp M., Pals A., Lille U. Eesti NSV Tead. Akad. Toim., Keem. 29:1980;191-195.
31. Berk S.C., Chang P.Y., Jeong N., Knochel P. Organometallics. 9:1990;3053-3064.
32. Berk S.C., Knochel P., Chang P.Y. J. Org. Chem. 53:1988;5789-5791.
33. Dieter R.K., Topping C.M., Chandupatla K.R., Lu K. J. Am. Chem. Soc. 123:2001;5132-5133.
34. +) calcd: 305.0964, found: 305.0968.
35. Rozema M.J., Sidduri A., Knochel P. J. Org. Chem. 57:1992;1956-1958.
36. Knochel P., Singer R.D. Chem. Rev. 93:1993;2117-2188.
37. ++Na) calcd: 346.0962, found: 346.0966.
38. 5 and 10% NOEs between the vinyl proton and the two protons of the side chain were observed, respectively.
39. See: Liu, J. J.; Konzelmann, F.; Luk, K. C. Tetrahedron Lett. 2003, 44, 2545-2548, Ref. 10.
40. Dieter R.K., Silks L.A. III. J. Org. Chem. 51:1986;4687.
41. For references on the mechanism of organocuprate conjugated additions, see: (a) Woodward, S. Chem. Soc. Rev. 2000, 29, 393-401; (b) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900; (c) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135; (d) Organocopper Reagents, A Practical Approach; Taylor, R. K., Ed.: Oxford University Press: Oxford, 1994; (e) Ullenius, C.; Christenson, B. Pure Appl. Chem. 1988, 60, 57; (f) Hallnemo, G.; Olsson; Ullenius, C. J. Organomet. Chem. 1985, 282, 133.
42. For references on the mechanism of organocuprate conjugated additions, see: (a) Woodward, S. Chem. Soc. Rev. 2000, 29, 393-401; (b) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900; (c) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135; (d) Organocopper Reagents, A Practical Approach; Taylor, R. K., Ed.: Oxford University Press: Oxford, 1994; (e) Ullenius, C.; Christenson, B. Pure Appl. Chem. 1988, 60, 57; (f) Hallnemo, G.; Olsson; Ullenius, C. J. Organomet. Chem. 1985, 282, 133.
43. For references on the mechanism of organocuprate conjugated additions, see: (a) Woodward, S. Chem. Soc. Rev. 2000, 29, 393-401; (b) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900; (c) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135; (d) Organocopper Reagents, A Practical Approach; Taylor, R. K., Ed.: Oxford University Press: Oxford, 1994; (e) Ullenius, C.; Christenson, B. Pure Appl. Chem. 1988, 60, 57; (f) Hallnemo, G.; Olsson; Ullenius, C. J. Organomet. Chem. 1985, 282, 133.
44. For references on the mechanism of organocuprate conjugated additions, see: (a) Woodward, S. Chem. Soc. Rev. 2000, 29, 393-401; (b) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900; (c) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135; (d) Organocopper Reagents, A Practical Approach; Taylor, R. K., Ed.: Oxford University Press: Oxford, 1994; (e) Ullenius, C.; Christenson, B. Pure Appl. Chem. 1988, 60, 57; (f) Hallnemo, G.; Olsson; Ullenius, C. J. Organomet. Chem. 1985, 282, 133.
45. For references on the mechanism of organocuprate conjugated additions, see: (a) Woodward, S. Chem. Soc. Rev. 2000, 29, 393-401; (b) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900; (c) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135; (d) Organocopper Reagents, A Practical Approach; Taylor, R. K., Ed.: Oxford University Press: Oxford, 1994; (e) Ullenius, C.; Christenson, B. Pure Appl. Chem. 1988, 60, 57; (f) Hallnemo, G.; Olsson; Ullenius, C. J. Organomet. Chem. 1985, 282, 133.
46. For references on the mechanism of organocuprate conjugated additions, see: (a) Woodward, S. Chem. Soc. Rev. 2000, 29, 393-401; (b) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900; (c) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135; (d) Organocopper Reagents, A Practical Approach; Taylor, R. K., Ed.: Oxford University Press: Oxford, 1994; (e) Ullenius, C.; Christenson, B. Pure Appl. Chem. 1988, 60, 57; (f) Hallnemo, G.; Olsson; Ullenius, C. J. Organomet. Chem. 1985, 282, 133.
47. There was no change on TLC after 8 or 11 was added to the THF solution of a Grignard reagent such as EtMgBr at -15°C and when the reaction mixture was finally heated up to reflux for 2 h the starting material decomposed.