Regioselective synthesis of pyrone-annulated sulfur heterocycles by aryl radical cyclization

Synthesis

Volumn , Issue 16, 2006, Pages 2725-2730

  Majumdar, K C ^a   Muhuri, S ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

4 mercapto 6 methyl pyran 2 one; 6 endo cyclization; Azobisisobutyronitrile; thio Claisen rearrangement; Tri n butyltin hydride

Indexed keywords

KETONES; SINGLE CRYSTALS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

ARYL RADICAL CYCLIZATION; AZOBISISOBUTYRONITRILE; HETEROCYCLES; THIO-CLAISEN REARRANGEMENT;

SULFUR;

4 (2' BROMOPHENOXYMETHYL) 7 METHYLTHIOPYRANO[3,2 C]PYRAN 5 ONE DERIVATIVE; 4 (4' ARYLOXYBUT 2' YNYL) 6 METHYL PYRAN 2 ONE DERIVATIVE; 4 MERCAPTO 6 METHYL PYRAN 2 ONE; AZOBISISOBUTYRONITRILE; BENZOPYRANO[4,3 C] 6A,12A DIHYDRO 3 METHYLTHIO PYRANOPYRAN 1 ONE DERIVATIVE; BUTYLTIN DERIVATIVE; BUTYLTIN HYDRIDE; HETEROCYCLIC COMPOUND; NITRILE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAN DERIVATIVE; PYRONE DERIVATIVE; SULFUR; TETRACYCLIC [6,6]PYRANOTHIOPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; CYCLIZATION; RADICAL REACTION; SYNTHESIS; X RAY ANALYSIS;

EID: 33748305986     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942499     Document Type: Article

References (36)

1. (a) Giese, B. Radicals in Organic Synthesis, Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986.
2. (b) Curran, D. P. Synthesis 1988, 417.
3. (c) Curran, D. P. Synthesis 1988, 489.
4. (d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
5. (e) Radicals in Organic Synthesis, Vol. 1; Renaud, P.; Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001.
6. (f) Radicals in Organic Synthesis, Vol. 2; Renaud, P.; Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001.
7. (a) Mors, W. B.; Gollilieb, O. R.; Djerassi, C. J. Am. Chem. Soc. 1957, 79, 4507.
8. (b) McGahren, W. J.; Ellestad, G. A.; Morton, G. O.; Kunstman, M. P.; Mullen, P. J. Org. Chem. 1973, 38, 3542.
9. (c) Sparace, S. A.; Mudd, J. B.; Bruke, B. A.; Aasan, A. J. Phytochemistry 1984, 23, 2693.
10. (d) Mori, K.; Otsuka, T.; Oda, M. Tetrahedron Lett. 1984, 40, 2929.
11. (e) Capon, R. J.; Faulkner, D. J. J. Org. Chem. 1984, 45, 2506.
12. (f) Ichihara, A.; Murakami, K.; Sakamura, S. Tetrahedron 1987, 43, 5245.
13. (g) Prasad, J. V. N.; Para, K. S.; Lunney, E. A.; Ortwine, D. E.; Dunbar, J. B. Jr.; Ferguson, D.; Tummino, P. J.; Hupe, D.; Bradley, B. D. J. Am. Chem. Soc. 1994, 116, 6989.
14. (a) Irschik, H.; Gerth, K.; Hofle, G.; Kohl, W.; Reichenbach, H. J. Antibiotics. 1983, 36, 16-51.
15. (b) Prasad, J. V. N.; Pavolovsky, P.; Para, K. S.; Ellsworth, E. L.; Tummino, P. J.; Nouhan, C.; Ferguson, D. Bioorg. Med. Chem. Lett. 1996, 6, 1113.
16. (a) Majumdar, K. C.; Chatterjee, P.; Saha, S. Tetrahedron Lett. 1998, 39, 7147.
17. (b) Majumdar, K. C.; Chatterjee, P.; Saha, S.; Samanta, S. K. Indian J. Chem., Sect. B.: Org. Chem. Incl. Med. Chem. 2001, 40, 915.
18. Majumdar, K. C.; Kundu, U. K.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 2002, 2139.
19. (a) Majumdar, K. C.; Kundu, U. K.; Ghosh, S. K. Org. Lett. 2002, 4, 2629.
20. (b) Majumdar, K. C.; Das, U. J. Org. Chem. 1998, 63, 9997.
21. (a) Shankaran, K.; Solan, C. P.; Snieckus, V. Tetrahedron Lett. 1985, 26, 6001.
22. (b) Solan, C. P.; Cuevas, J. C.; Quesnelle, C.; Snieckus, V. Tetrahedron Lett. 1988, 29, 4685.
23. (c) Parker, K. A.; Spero, D. M.; Inman, K. C. Tetrahedron Lett. 1986, 27, 2833.
24. (d) Jones, K.; Willkinson, J. A. J. Chem. Soc., Chem. Commun. 1992, 1767.
25. (a) Ishibashi, H.; Kato, I.; Takeda, Y.; Kogure, M.; Tamura, O. J. Chem. Soc., Chem. Commun. 2000, 1527.
26. (b) Ponaras, A. A.; Zaim, O. Tetrahedron Lett. 2000, 41, 2279.
27. (c) Cid, M. M.; Dominguez, D.; Castedo, L.; Va'zquez-Lopez, E. M. Tetrahedron 1999, 55, 5599.
28. Ishibashi, H.; Kawanami, H.; Nakagawa, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 2291.
29. Abeywickrema, A. N.; Beckwith, A. L. J.; Gerba, S. J. Org. Chem. 1987, 52, 4072.
30. (a) Enholm, E. J.; Prasad, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784.
31. (b) Enholm, E. J.; Kinter, K. S. J. Org. Chem. 1995, 60, 4850.
32. (a) SAINT, Program for Area Detector Absorption Correction; Siemens Analytical X-ray Instruments Inc.: Madison, WI 53719, USA, 1994-1996.
33. (b) Sheldrick, G. M. SHELXS-97, A Program for Crystal Structure Solution; University of Gottingen: Germany, 1997.
34. Sheldrick, G. M. SADABS, Program of Siemens Area Detector Absorption Correction; University of Gottingen: Germany, 1996.
35. Spek, A. L. PLATON; University of Utrecht: The Netherlands, 2001.
36. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.