Novel formation of iodobenzene derivatives from 1-(methylthio)-3-tosylhexa- 1,3-dien-5-ynes via iodine-induced intramolecular cyclization

Journal of Organic Chemistry

Volumn 73, Issue 5, 2008, Pages 1726-1731

  Matsumoto, Shoji ^a   Takase, Kenji ^a   Ogura, Katsuyuki ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INTRAMOLECULAR CYCLIZATION; IODOBENZENE DERIVATIVES;

CYCLIZATION; DERIVATIVES; ISOMERIZATION; SYNTHESIS (CHEMICAL); ULTRAVIOLET RADIATION;

BENZENE;

1 (METHYLTHIO) 3 TOSYLHEXA 1,3 DIEN 5 YNE; 1 (METHYLTHIO) 6 PHENYL 3 TOSYLHEXA 1,3 DIEN 5 YNE; IODINE; IODOBENZENE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET IRRADIATION;

EID: 41149135494     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701976q     Document Type: Article

References (47)

1. (a) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: Chichester, UK, 1999.
2. (b) Suzuki, A.; Brown H. C. Organic Synthesis via Boranes: Suzuki Coupling; Aldrich Chemical Co. Inc.: Milwaukee, WI, 2003; Vol. 3.
3. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
4. (d) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469.
5. (e) Corbet, J. -P.; Mignani, G. Chem. Rev. 2006, 106, 2651-2710.
6. (a) Seevers, R. H.; Counsell, R. E. Chem. Rev. 1982, 82, 575-590.
7. (b) Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253-6254.
8. (c) Swenton, J. S.; Callinan, A.; Wang, S. J. Org. Chem. 1992, 57, 78-85.
9. (d) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1993, 32, 1377-1385.
10. (e) Tatko, C. D.; Waters, M. L. Org. Lett. 2004, 6, 3969-3972.
11. Review: (a) Merkushev, E. B. Synthesis 1988, 923-937. Recent reports:
12. (b) Yang, S. G.; Kim, Y. H. Tetrahedron Lett. 1999, 40, 6051-6054.
13. (c) Branytska, O. V.; Neumann, R. J. Org. Chem. 2003, 68, 9510-9512.
14. (d) Adimurthy, S.; Ramachandraiah, G.; Ghosh, P. K.; Bedekar, A. V. Tetrahedron Lett. 2003, 44, 5099-5101.
15. (e) Ghorbani-Vaghei, R. Tetrahedron Lett. 2003, 44, 7529-7532.
16. (f) Alexander, V. M.; Khandekar, A. C.; Samant, S. D. Synlett 2003, 1895-1897.
17. (g) Iskra, J.; Stavber, S.; Zupan, M. Synthesis 2004, 1869-1873.
18. (h) Wan, S.; Wang, S. R.; Lu, W. J. Org. Chem. 2006, 71, 4349-4352.
19. Tinnemans, A. H. A.; Laarhoven, W. H. Tetrahedron Lett. 1973, 817-820.
20. Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518-519.
21. Shen, H.-C.; Pal, S.; Lian, J.-J.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 15762-15763.
22. Yamamoto, Y.; Hattori, K.; Nishiyama, H. J. Am. Chem. Soc. 2006, 128, 8336-8340.
23. (a) Goldfinger, M. B.; Swager, T. M. J. Am. Chem. Soc. 1994, 116, 7895-7896.
24. (b) Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 4578-4593.
25. (c) Yao, T.; Campo, M. A.; Larock, R. C. J. Org. Chem. 2005, 70, 3511-3517.
26. (d) Zhang, X.; Sarkar, S.; Larock, R. C. J. Org. Chem. 2006, 71, 236-243.
27. (e) Barluenga, J.; Vázquez-Villa, H.; Merino, I.; Ballesteros, A.; González, J. M. Chem. - Eur. J. 2006, 12, 5790-5805.
28. (f) Yue, D.; Cá, N. D.; Larock, R. C. J. Org. Chem. 2006, 71, 3381-3388.
29. (a) Matsumoto, S.; Takahashi, S.; Ogura, K. Heteroat. Chem. 2001, 12, 385-391.
30. (b) Matsumoto, S.; Kumazawa, K.; Ogura, K. Bull. Chem. Soc. Jpn. 2003, 76, 2179-2182.
31. Ogura, K.; Takeda, M.; Xie, J. R.; Akazome, M.; Matsumoto, S. Tetrahedron Lett. 2001, 42, 1923-1925.
32. The geometry of the C-C double bond at the 1,2-position in 8 was determined using NOE measurements. (Chemical Equation Presented)
33. Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292-10296.
34. (a) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409.
35. (b) Amjad, M.; Knight, D. W. Tetrahedron Lett. 2004, 45, 539-541.
36. (c) Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2006, 71, 62-69.
37. (d) Hessian, K. O.; Flynn, B. L. Org. Lett. 2006, 8, 243-246.
38. (a) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651-654.
39. (b) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905-1909.
40. (c) Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377-4380.
41. (a) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437-3444.
42. (b) Zhang, X.; Campo, M. A.; Yao, T.; Larock, R. C. Org. Lett. 2005, 7, 763-766.
43. (c) Kesharwani, T.; Worlikar, S. A.; Larock, R. C. J. Org. Chem. 2006, 71, 2307-2312.
44. (d) Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2007, 46, 4764-4766.
45. Field, L.; Vanhorne, J. L.; Cunningham, L. W. J. Org. Chem. 1970, 35, 3267-3273.
46. With MOPAC 97; Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-220.
47. Ogura, K.; Iihama, T.; Takahashi, K.; Iida, H. Bull. Chem. Soc. Jpn. 1984, 57, 3347-3348.