Electrophilic cyclization of buta-1,3-diynylarenes: Synthesis of precursors of (z)-3-ene-1,5-diyne systems fused to heterocycles

Synlett

Volumn , Issue 4, 2011, Pages 517-520

  Danilkina, Natalia A ^a   Bräse, Stefan ^b   Balova, Irina A ^a  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

^b UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

alkynes; electrophilic cyclization; enediynes; heterocycles

Indexed keywords

2 ETHYNYL 3 IODO BENZOTHIOPHENE DERIVATIVE; BENZOFURAN DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; BUTA 1,3 DIYNYL ARENE DERIVATIVE; FUSED HETEROCYCLIC RINGS; INDOLE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPOSITE MATERIAL; CYCLIZATION; ELECTROPHILIC CYCLIZATION; PROCESS DEVELOPMENT; SYNTHESIS;

EID: 79951853317     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259547     Document Type: Article

References (52)

1. (a) Larock, R. C. In Acetylene Chemistry; Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, 2005, 51-99.
2. (b) Mehta, S.; Larock, R. C. J. Org. Chem. 2010, 75, 1652; and references cited therein.
3. (c) Manarin, F.; Roehrs, J. A.; Brandão, R.; Nogueira, C. W.; Zeni, G. Synthesis 2009, 4001.
4. (d) Cho, C.-H.; Neuenswander, B.; Larock, R. C. J. Comb. Chem. 2010, 12, 278.
5. (e) Worlikar, S. A.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Comb. Chem. 2009, 11, 875.
6. (f) Cho, C.-H.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Comb. Chem. 2009, 11, 900.
7. (g) Manarin, F.; Roehrs, J. A.; Gay, R. M.; Brandao, R.; Menezes, P. H.; Nogueira, C. W.; Zeni, G. J. Org. Chem. 2009, 74, 2153.
8. (h) Mehta, S.; Waldo, J. P.; Larock, R. C. J. Org. Chem. 2009, 74, 1141.
9. (i) Cho, C.-H.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Comb. Chem. 2008, 10, 941.
10. (a) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905.
11. (b) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651.
12. (c) Yue, D.; Larock, R. C. Tetrahedron Lett. 2001, 42, 6011.
13. (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432.
14. (b) Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292.
15. (c) Okitsu, T.; Nakazawa, D.; Taniguchi, R.; Wada, A. Org. Lett. 2008, 10, 4967.
16. (a) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem. Int. Ed. 2003, 42, 2406.
17. (b) Amjad, M.; Knight, D. W. Tetrahedron Lett. 2004, 45, 539.
18. (c) Yue, D.; Larock, R. C. Org. Lett. 2004, 6, 1037.
19. (d) Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2006, 71, 62.
20. (a) Wei, S.; Coleman, R. S.; Lowary, T. L. Org. Biomol. Chem. 2009, 7, 3709.
21. (b) Santin, E. P.; Khanwalkar, H.; Voegel, J.; Collette, P.; Mauvais, P.; Gronemeye, H.; de Lera, A. R. ChemMedChem 2009, 4, 780.
22. (c) Yang, L.-Y.; Chang, C.-F.; Huang, Y.-C.; Lee, Y.-J.; Hu, C.-C.; Tseng, T.-H. Synthesis 2009, 1175.
23. (d) Bang, H. B.; Han, S. Y.; Choi, D. H.; Yang, D. M.; Hwang, J. W.; Lee, H. S.; Jun, J.-G. Synth. Commun. 2009, 39, 506.
24. (a) Zhou, Y.; Liu, W.-J.; Ma, Y.; Wang, H.; Qi, L.; Cao, Y.; Wang, J.; Pei, J. J. Am. Chem. Soc. 2007, 129, 12386.
25. (b) Kobayashi, T.; Hasegawa, Y. US 2005258398, 2005.
26. Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem. Int. Ed. 2003, 42, 2406.
27. (a) Vinogradova, O. V.; Sorokoumov, V. N.; Vasylevsky, S. F.; Balova, I. A. Tetrahedron Lett. 2007, 48, 4907.
28. (b) Vinogradova, O. V.; Sorokoumov, V. N.; Balova, I. A. Tetrahedron Lett. 2009, 50, 6358.
29. (a) Sahu, B.; Namboothiri, I. N. N.; Persky, R. Tetrahedron Lett. 2005, 46, 2593.
30. (b) Sahu, B.; Muruganantham, R.; Namboothiri, I. N. N. Eur. J. Org. Chem. 2007, 2477.
31. (a) Kim, C.-S.; Russell, K. C. J. Org. Chem. 1998, 63, 8229.
32. (b) Kumarasinghe, E. S.; Peterson, M. A.; Robins, M. J. Tetrahedron Lett. 2000, 41, 8741.
33. For recent reviews, see: (a) Jones, G. B.; Fouad, F. S. Curr. Pharm. Des. 2002, 8, 2415.
34. (b) Maretina, I. A.; Trofimov, B. A. Russ. Chem. Rev. 2006, 75, 825.
35. (c) Shao, R.-G. Curr. Mol. Pharm. 2008, 1, 50.
36. (a) Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron 2008, 64, 53.
37. (b) Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron 2008, 64, 7301.
38. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
39. (b) Balova, I. A.; Sorokoumov, V. N.; Morozkina, S. N.; Vinogradova, O. V.; Knight, D. W.; Vasilevsky, S. F. Eur. J. Org. Chem. 2005, 882.
40. (c) Liang, Y.; Tao, L.-M.; Zhang, Y.-H.; Li, J.-H. Synthesis 2008, 3988.
41. 3, 400 MHz, TMS as reference).
42. (a) Sooloki, D.; Kennedy, V. O.; Tessier, C. A.; Youngs, W. J. Synlett 1990, 427.
43. (b) Sooloki, D.; Bradshaw, J. D.; Tessier, C. A.; Youngs, W. J. Organometallics 1994, 13, 451.
44. It was determined by TLC that O-benzyl-2-(dodeca-1,3- diynyl)phenol reacts with ICl in MeCN in similar way giving benzofuran 3i with iodochlorinated triple bond.
45. Ebata, H.; Miyazaki, E.; Yamamoto, T.; Takimiya, K. Org. Lett. 2007, 9, 4499.
46. (a) Barluenga, J.; Fananas-Mastral, M.; Andina, F.; Aznar, F.; Valdes, C. Organometallics 2008, 27, 3593.
47. (b) Kitagaki, S.; Katoh, K.; Ohdachi, K.; Takahashi, Y.; Shibata, D.; Mukai, C. J. Org. Chem. 2006, 71, 6908.
48. (c) Shvartsberg, M. S.; Vasilevskii, S. F.; Prihod'ko, T. A. Izv. Acad. Nauk SSSR, Ser. Khim. 1982, 11, 2524.
49. 4, and concentrated under reduced pressure to yield the crude product, which was purified by column chromatography on silica gel using pentane (for 2a,b,d,e,g) or cyclohexane-EtOAc (2c,f) as the eluent.
50. 9OSI: C, 43.92; H, 2.76; S, 9.77. Found: C, 43.85; H, 2.69; S, 9.61.
51. 4, and concentrated under reduced pressure to yield the crude product, which was purified by column chromatography on silica gel using pentane (for 4a,c,d,h,i) or cyclohexane-EtOAc (for 4b,e-g) as the eluent.
52. 18OSSi: 298.0848; found: 298.0845.