Preparation of N-alkylated pyridones via selective N-alkylation of 2-alkoxypyridines on solid phase

Journal of Combinatorial Chemistry

Volumn 4, Issue 5, 2002, Pages 530-535

  Ruda, Marcus C ^a,b   Bergman, Jan ^b,c   Wu, Jinchang ^a  

^a Karo Bio   (Sweden)

^b KAROLINSKA INSTITUTE   (Sweden)

^c SÖDERTÖRN UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0040675423     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc020036i     Document Type: Article

References (17)

1. Morzycki, J. W. Partial Synthesis of Azasteroids. Pol. J. Chem. 1995, 69, 321-340.
2. Huisman, H. O. Approaches to Total Synthesis of Heterocyclic Steroidal Systems. Angew. Chem., Int. Ed. Engl. 1971, 10, 450-459.
3. Morand, P.; Lyall, J. The Steroidal Estrogens. Chem. Rev. 1968, 68, 85-124.
4. Rasmusson, G. H.: Reynolds, G. F.; Utne. T.; Jobson, R. B.; Primka. R. L.: et al. Azasteroids as Inhibitors of Rat Prostatic 5α-Reductase. J. Med. Chem. 1984, 27, 1690-1701.
5. Josein, H.; Ko, S.-B.; Bom, D.; Curran, D. P. A General Synthetic Approach to the (20S)-Camptothecin Family of Antitumor Agents by a Regiocontrolled Cascade Radical Cyclization of Aryl Isonitriles. Chem.-Eur. J. 1998, 4, 67-83.
6. Comins, D. L.; Nolan, J. M. A Practical Six-Step Synthesis of (S)-Camptothecin. Org. Lett. 2001, 3, 4255-4257.
7. Hong, H.; Comins, D. L. A three-step synthesis of Cerpegin. J. Org. Chem. 1996, 61, 391-392.
8. Kelly, T. R.; Walsh, J. J. The Synthesis of Cerpegin. J. Org. Chem. 1992, 57, 6657-6658.
9. Guillier, F.; Nivoliers, F.; Bourguignon, J.; Dupas, G.; Marsais, F.; et al. Metalation of Pi-Deficient Heterocycles, a Facile Synthesis of Cerpegin. Tetrahedron Lett. 1992, 33, 7355-7356.
10. Liu, H.; Ko, S. B.; Josien, H.; Curran, D. P. Selective N-Functionalization of 6-Substituted-2-Pyridones. Tetrahedron Lett. 1995, 36, 8917-8920.
11. Sato, T.; Yoshimatsu, K.; Otera, J. CsF in Organic Synthesis. Tuning of N-or O-Alkylation of 2-Pyridone. Synlett 1995, 845-846.
12. Bowman W. R.; Bridge, C. F. Regioselective synthesis of N-alkyl pyridones. Synth. Commun. 1999, 29, 4051-4059.
13. Mohan, R.; Yun, W. Y.; Buckman, B. O.; Liang, A.; Trinh, L.; et al. Solid-phase synthesis of N-substituted amidinophenoxy pyridines as factor Xa inhibitors. Bioorg. Med. Chem. Lett. 1998, 8, 1877-1882.
14. Chen, C. X.; Munoz, B. Solid phase synthesis of N-acyl-2-substituted-dihydro-4-pyridone: Resin activation capture approach REACAP technology. Tetrahedron Lett. 1998, 39, 6781-6784.
15. Comins, D. L.; Gao, J. H. N-vs. O-Alkylation in the Mitsunobu Reaction of 2-Pyridone. Tetrahedron Lett. 1994, 35, 2819-2822.
16. Hodge, P. Polymer-supported organic reaction: what takes place in the beads? Chem. Soc. Rev 1997, 27, 417-424.
17. Chung N M.; Tieckelmann, H. Alkylations of Heterocyclic Ambident Anions. IV. Alkylation of 5-Carbethoxy- and 5-Nitro-2-pyridone Salt. J. Org. Chem. 1970, 35, 2517-2520.