A convenient method for the preparation of 4-hydroxy-2-methyl-1-oxo-1,2- dihydroisoquinoline-3-carboxylic acid derivatives

Synthesis

Volumn , Issue 12, 2006, Pages 1971-1974

  Blanco, María Mercedes ^a   Shmidt, María Sol ^a   Schapira, Celia Beatriz ^a   Perillo, Isabel Amalia ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Cyclization; Enols; Heterocycles; Isoquinolinones; Lactams

Indexed keywords

ACETIC ACID; CATALYSIS; CONDENSATION; CONDENSATION REACTIONS; DERIVATIVES; SYNTHESIS (CHEMICAL);

CYCLIZATION; ENOLS; HETEROCYCLES; ISOQUINOLINONES; LACTAMS;

CARBOXYLIC ACIDS;

2 TERT BUTYL 4 HYDROXY N METHYL 1 OXO N PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXAMIDE; 4 HYDROXY 2 METHYL 1 OXO 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC ACID DERIVATIVE; 4 HYDROXY 2 METHYL 1 OXO 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC ETHYL ESTER; 4 HYDROXY 2 METHYL 1 OXO 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC METHYL ESTER; 4 HYDROXY 2 METHYL 1 OXO N PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXAMIDE; 4 HYDROXY N,2 DIMETHYL 1 OXO N PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXAMIDE; AMIDE; CARBOXYLIC ACID DERIVATIVE; DIAZOMETHANE; ESTER DERIVATIVE; GLYCINE DERIVATIVE; N,N DIETHYL 4 HYDROXY 2 METHYL 1 OXO 1,2 DIHYDROISOQUINOLINE 3 CARBOXAMIDE; PHTHALAMIC ESTER; PHTHALIC ANHYDRIDE; UNCLASSIFIED DRUG;

AMINOLYSIS; ARTICLE; CYCLIZATION; DIECKMANN REACTION; DRUG SYNTHESIS; ESTERIFICATION;

EID: 33745754936     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942402     Document Type: Article

References (31)

1. Among others: (a) Khan, S. R.; Mhaka, A.; Pili, R.; Isaacs, J. T. Bioorg. Med. Chem. Lett. 2001, 11, 451.
2. (b) Shi, J.; Xiao, Z.; Ihnat, M. A.; Kamat, C.; Pandit, B.; Hu, Z.; Li, P. K. Bioorg. Med. Chem. Lett. 2003, 13, 1187.
3. (c) Jönsson, S.; Andersson, G.; Fex, T.; Fristedt, T.; Hedlund, G.; Jansson, K.; Abramo, L.; Fritzson, I.; Pekarski, O.; Runström, A.; Sandin, H.; Thuvesson, I.; Björk, A. J. Med. Chem. 2004, 47, 2075; and references cited therein,
4. (d) Brunmark, C.; Runström, A.; Ohlsson, L.; Sparre, B.; Brodin, T.; Aström, M.; Hedlund, G. J. Neuroimmunol. 2002, 130, 163.
5. (e) Tsuji, K.; Spears, G. W.; Nakamura, K.; Tojo, T.; Seki, N.; Sugiyama, A.; Matsuo, M. Bioorg. Med. Chem. Lett. 2002, 12, 85.
6. (f) Folkes, A.; Brown, S. D.; Canne, L. E.; Chan, J.; Engelhardt, E.; Epshteyn, S.; Faint, R.; Golec, J.; Hanel, A.; Kearney, P.; Leahy, J. W.; Mac, M.; Matthews, D.; Prisbilla, M. P.; Sanderson, J.; Simon, R. J.; Tesfai, Z.; Vicker, N.; Wang, S.; Webb, R. R.; Charlton, P. Bioorg. Med. Chem. Lett. 2002, 12, 1063.
7. (g) Ukrainets, I. V.; Taran, S. G.; Gorokhova, O. V.; Taran, E. A.; Jaradat, N. A.; Petukhova, I. Y. Chem. Heterocycl. Compd. (Engl. Transl.) 2000, 36, 166.
8. (h) Ukrainets, I. V.; Taran, S. G.; Likhanova, N. V.; Rybakov, V. B.; Gorokhova, O. V.; Jaradat, N. A. Chem. Heterocycl. Compd. (Engl. Transl.) 2000, 36, 49.
9. Kugalowski, J. J.; Baker, R.; Curtis, N. R.; Leeson, P. D.; Mawer, I. M.; Moseley, A. M.; Ridgill, M. P.; Rowley, M.; Stansfield, I.; Foster, A. C.; Grimwood, S.; Hill, R. G.; Kemp, J. A.; Marshall, J. R.; Saywell, K. L.; Tricklebank, M. D. J. Med. Chem. 1994, 37, 1402.
10. Among others, see: (a) Lombardino, J. G. J. Heterocycl. Chem. 1970, 7, 1057.
11. (b) Schapira, C. B.; Abasolo, M. I.; Perillo, I. A. J. Heterocycl. Chem. 1985, 22, 577; and references cited therein.
12. (c) Kadin, S. B.; Wiseman, E. H. Nature 1969, 222, 275.
13. (d) Lazer, E.; Miao, C. K.; Cywin, C. L.; Sorcek, R.; Wong, H.-C.; Meng, Z.; Potocki, I.; Hoermann, M.; Snow, R. J.; Tschantz, M. A.; Kelly, T. A.; McNeil, D. W.; Coutts, S. J.; Churchill, L.; Graham, V.; David, E.; Grob, P. M.; Engel, W.; Meier, H.; Trummlitz, G. J. Med. Chem. 1997, 40, 980.
14. Among others, see: (a) Blanco, M. M.; Schapira, C. B.; Levin, G.; Perillo, I. A. J. Heterocycl. Chem. 2005, 42, 493; and references cited therein.
15. (b) Scotese, A. C.; Santilli, A. A. S. African ZA 8000631, 1981; Chem. Abstr. 1982, 96, 6706.
16. (c) Scotese, A. C.; Morris, R. L.; Santilli, A. A. US Patent 4301281, 1981; Chem. Abstr. 1982, 97, 23815.
17. (d) Armitage, B. J.; Leslie, B. W. PCT Int. Appl. WO 9611199, 1996; Chem. Abstr. 1996, 125, 114712.
18. (e) Nuebling, C.; Von Deyn, W.; Theobald, H.; Westphalen, K.-O.; Kardorff, U.; Helmut, W.; Kappe, T.; Gerber, M. Ger. Offen. DE 4227747, 1993; Chem. Abstr. 1994, 120, 323554z.
19. Among others, see: (a) Toyama, M.; Otomasu, H. Chem. Pharm. Bull. 1985, 33, 5543.
20. (b) Alonso-Silva, I. J.; Pardo, M.; Soto, J. L. Heterocycles 1988, 27, 357.
21. (c) Beattie, J. F.; Hales, N. J. J. Chem. Soc., Perkin Trans, 1 1992, 751.
22. (d) Khalaj, A.; Adibpour, N. Heterocycles 1999, 51, 131.
23. (a) Suzuki, M.; Nunami, K.; Matsumoto, K.; Yoneda, N.; Miyoshi, M. Synthesis 1978, 461.
24. (b) Nunami, K.; Suzuki, M.; Matsumoto, K.; Miyoshi, M.; Yoneda, N. Chem. Pharm. Bull. 1979, 27, 1373.
25. (c) Miyoshi, S.; Yoneda, N.; Matsumoto, K.; Suzuki, M.; Nunami, K. Jpn. Kokai Tokkio Koho 7970285, 1979; Chem. Abstr. 1979, 91, 175221.
26. Ease of trans-esterification is related to the presence of an electron-withdrawing group at the α-position to the ester (ref. 7) and it was also observed in Dieckmann cyclizations which lead to hydroxy derivatives of related heterocycles (ref. 8).
27. Janczewski, D.; Synoradzki, L.; Wlostowski, M. Synlett 2003, 420.
28. Blanco, M. M.; Perillo, I. A.; Schapira, C. B. J. Heterocycl. Chem. 1999, 36, 979; and references cited therein.
29. This fact is related to the acid character of aniline hydrogen in phthalamic ester 2c which would allow its deprotonation in basic medium, thus resulting in a less probable formation of the carbanion necessary for the heterocyclization. A similar behavior was observed in the alkoxide promoted cyclization of compounds structurally related to 2c (ref. 3a).
30. 2O, mp 195-197 °C.
31. The nonresolved multiplicity of the methylene and methyl signals is related to stereochemical features of this type of amides: partial double bond character of CO-N amide bond and/or the diastereotopicity of the methylene hydrogens associated with the presence of a chiral axis (ref. 4a).