Synthesis of 2-(arylsulfonyl)-4-hydroxypyridines by Hetero-Diels-Alder reaction of 1,3-bis-silyl enol ethers with arylsulfonyl cyanides

Synthesis

Volumn , Issue 15, 2006, Pages 2551-2555

  Emmrich, Thomas ^a   Reinke, Helmut ^b   Langer, Peter ^b  

^a UNIVERSITY OF GREIFSWALD   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

1,3 bis silyl enol ethers; Arylsulfonyl cyanide; Hetero Diels Alder; Pyridine

Indexed keywords

ALCOHOLS; ETHERS; RATE CONSTANTS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

1,3-BIS-SILYL ENOL ETHERS; ARYLSULFONYL CYANIDE; HETERO-DIELS-ALDER; PYRIDINE;

NITROGEN COMPOUNDS;

1,3 BIS SILYL ENOL ETHER DERIVATIVE; 1,3 BIS(TRIMETHYLSILOXY)BUTA 1,3 DIENE DERIVATIVE; 2 (ARYLSULFONYL) 4 HYDROXYPYRIDINE DERIVATIVE; 4 ARYL 2 (ARYLSULFONYL)PYRIDINE DERIVATIVE; ALKADIENE; ARYLSULFONYL CYANIDE DERIVATIVE; CYANIDE; ETHER DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDINOL; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 33747191495     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942446     Document Type: Article

References (22)

1. (a) Boger, D. L.; Weinreb, S. M. Hetero-Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego CA, 1987.
2. (b) Tietze, L. F.; Schneider, C. J. Org. Chem. 1991, 56, 2476.
3. For cycloaddition reactions of nitriles, see: Collier, S.; Langer, P. In Science of Synthesis; Shinkai, I.; Murahashi, S., Eds.; Thieme: Stuttgart, 2004, Chap. 19.5.15.
4. Breitmaier, E.; Rüffer, U. Synthesis 1989, 623.
5. Sulfonyl cyanides have been used as electrophilic cyanation reagents, see: (a) Christophersen, C.; Begrup, M.; Ebdrup, S.; Petersen, H.; Vedsoe, P. J. Org. Chem. 2003, 68, 9513.
6. (b) Boymond, L.; Rottlaender, M.; Cahiez, G.; Knochel, P. Angew. Chem. Int. Ed. 1998, 37, 1701.
7. (c) Jensen, T.; Teiler, J.; Waernmark, K. J. Org. Chem. 2002, 67, 6008.
8. Wang, T.; Hendrickson, J. Org. Prep. Proced. Int. 2003, 35, 623.
9. van Leusen, A. M.; Jagt, J. C.
10. McClure, C. K.; Link, J. S. J. Org. Chem. 2003, 68, 8256.
11. For a review of 1,3-bis-silyl enol ethers, see: Langer, P. Synthesis 2002, 441.
12. (a) Hirokawa, Y.; Horikawa, T.; Kato, S. Chem. Pharm. Bull. 2000, 48, 1847.
13. (b) Cutshall, N. S.; Ursino, R.; Kucera, K. A.; Latham, J.; Ihle, N. C. Bioorg. Med. Chem. Lett. 2001, 14, 1951.
14. (c) Bonnet, V.; Mongin, F.; Trecourt, F.; Queguiner, G.; Knochel, P. Tetrahedron 2002, 58, 4429.
15. (d) Ohnmacht, C. J.; Russell, K.; Empfield, J. R.; Frank, C. A.; Gibson, K. H. J. Med. Chem. 1996, 39, 4592.
16. (e) Yogi, S.; Hokama, K.; Tsuge, O. Bull. Chem. Soc. Jpn. 1987, 60, 335.
17. (f) Reiffenrath, V.; Bremer, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1386;
18. Angew. Chem. 1994, 106, 1435.
19. (g) Furukawa, N.; Tsuruoka, M.; Fujihara, H. Heterocycles 1986, 24, 3337.
20. Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830.
21. Anderson, G.; Cameron, D. W.; Feutrill, G. I.; Read, R. W. Tetrahedron Lett. 1981, 22, 4347.
22. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-295095(3c) and CCDC-297417(3e). Copies of this data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk) or via www.ccdc.cam.ac.uk/conts/retrieving.html.