Convenient multigram synthesis of 4-chloropyridine-2,6-dicarbonyl dichloride

Synthesis

Volumn , Issue 5, 2009, Pages 713-714

  Mitsui, Kazuhiko ^a   Parquette, Jon R ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

4 chloropyridine 2; 6 dicarbonyl dichloride; Carboxylic acid chlorides; Deoxygenative chlorination; Nitrogen heterocycles; Supramo Lecular chemistry

Indexed keywords

4-CHLOROPYRIDINE-2; 6-DICARBONYL DICHLORIDE; CARBOXYLIC ACID CHLORIDES; DEOXYGENATIVE CHLORINATION; NITROGEN HETEROCYCLES; SUPRAMO- LECULAR CHEMISTRY;

CARBOXYLIC ACIDS; CHLORINATION; CHLORINE; CHLORINE COMPOUNDS; ORGANIC ACIDS;

SYNTHESIS (CHEMICAL);

4 CHLOROPYRIDINE 2,6 DICARBONYL DICHLORIDE; CARBONYL DERIVATIVE; PYRIDINE 1 OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHLORINATION; DEOXYGENATION; SYNTHESIS; TECHNIQUE;

EID: 63449097242     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1083348     Document Type: Article

References (27)

1. (a) Tse, M. K.; Bhor, S.; Klawonn, M.; Anilkumar, G.; Jiao, H.; Dobler, C.; Spannenberg, A.; Magerlein, W.; Hugl, H.; Beller, M. Chem. Eur. J. 2006, 12, 1855.
2. (b) Cornejo, A.; Fraile, J. M.; Garcia, J. I.; Gil, M. J.; Luis, S. V.; Martinez- Merino, V.; Mayoral, J. A. J. Org. Chem. 2005, 70, 5536.
3. (c) Barsu, C.; Fortrie, R.; Nowika, K.; Baldeck, P. L.; Vial, J.-C.; Barsella, A.; Fort, A.; Hissler, M.; Bretonniere, Y.; Maury, O.; Andraud, C. Chem. Commun. 2006, 4744.
4. (a) Hisamatsu, Y.; Hasada, K.; Amano, F.; Tsubota, Y.; Wasada-Tsutsui, Y.; Shirai, N.; Ikeda, S.; Odashima, K. Chem. Eur. J. 2006, 12, 7733.
5. (b) Chae, M. K.; Cha, G.-Y.; Jeong, K.-S. Tetrahedron Lett. 2006, 47, 8217.
6. (c) Haino, T.; Fujii, T.; Fukazawa, Y. J. Org. Chem. 2006, 71, 2572.
7. (d) Chang, S.-Y.; Kim, H. S.; Chang, K.-J.; Jeong, K.-S. Org. Lett. 2004, 6, 181.
8. (a) Hong, F.; Hollenback, D.; Singer, J. W.; Klein, P. Bioorg. Med. Chem. Lett. 2005, 15, 4703.
9. (b) Bhattacharya, S.; Snehalatha, K.; Kumar, V. P. J. Org. Chem. 2003, 68, 2741.
10. (c) Kurosaki, H.; Sharma, R. K.; Aoki, S.; Inoue, T.; Okamoto, Y.; Sugiura, Y.; Doi, M.; Ishida, T.; Otsuka, M.; Goto, M. J. Chem. Soc., Dalton Trans. 2001, 441.
11. (a) Gabriel, C. J.; Parquette, J. R. J. Am. Chem. Soc. 2006, 128, 13708.
12. (b) Huang, B.; Prantil, M. A.; Gustafson, T. L.; Parquette, J. R. J. Am. Chem. Soc. 2003, 125, 14518.
13. (c) Hofacker, A. L.; Parquette, J. R. Angew. Chem. Int. Ed. 2005, 44, 1053.
14. (a) Riegel, R.; Zwilgmeyer, D. Org. Synth. Coll. Vol. II 1950, 126.
15. (b) Fibel, L. R.; Spoerri, P. E. J. Am. Chem. Soc. 1948, 70, 3908.
16. (c) Toomey, R. F.; Riegel, E. R. J. Org. Chem. 1952, 17, 1492.
17. (d) Harirchain, B.; Gormley, J. L. US Patent 5300657, 1994; Chem. Abstr. 1994, 121, 9159.
18. (e) Horvath, G.; Rusa, C.; Kontos, Z.; Gerencser, J.; Huszthy, P. Synth. Commun. 1999, 29, 3719.
19. (a) Evans, R. F.; Brown, H. C. J. Org. Chem. 1962, 27, 1329.
20. (b) Hansen, J. F.; Kim, Y. I.; Merrigan, K. A. J. Org. Chem. 1979, 44, 4438.
21. (c) Bremner, D. H.; Dunn, A. D.; Wilson, K. A. Synthesis 1992, 6, 528.
22. (d) Alcazar, J.; Alonso, J. M.; Bartolome, J. M.; Iturino, L.; Matesanz, E. Tetrahedron Lett. 2003, 44, 8983.
23. (e) Thibault, C.; L'Heureux, A.; Bhide, R. S.; Ruel, R. Org. Lett. 2003, 5, 5023.
24. (a) Syper, L.; Kloc, K.; Mlochowski, J.; Szulc, Z. Synthesis 1979, 521.
25. (b) Thummel, R. P.; Chirayil, S.; Hery, C.; Lim, J.-L.; Wang, T.-L. J. Org. Chem. 1993, 58, 1666.
26. Recker, J.; Tomcik, D. J.; Parquette, J. R. J. Am. Chem. Soc. 2000, 122, 10298.
27. Markees, D. G. J. Org. Chem. 1958, 23, 1030.