Synthesis of heteroarylazulenes: transition metal free coupling strategy of azulene with heterocycles

Tetrahedron Letters

Volumn 48, Issue 7, 2007, Pages 1099-1103

  Shoji, Taku ^a   Yokoyama, Ryuji ^a   Ito, Shunji ^b   Watanabe, Masataka ^a   Toyota, Kozo ^a   Yasunami, Masafumi ^c   Morita, Noboru ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b HIROSAKI UNIVERSITY   (Japan)

^c NIHON UNIVERSITY   (Japan)

Author keywords

Azulene; Electrophilic substitution; Heterocycle

Indexed keywords

AZULENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM HYDROXIDE; TRANSITION ELEMENT; TRIFLUOROMETHANESULFONIC ACID;

AROMATIZATION; ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; REVERSED PHASE LIQUID CHROMATOGRAPHY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33846264599     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.083     Document Type: Article

References (22)

1. Craig P.N. In: Drayton C.J. (Ed). Comprehensive Medicinal Chemistry Vol. 8 (1991), Pergamon Press, New York
2. Southon I.W., and Buckingham J. In: Saxton J.E. (Ed). Dictionary of Alkaloids (1989), Chapman and Hall, London
3. Negwer M. Organic-Chemical Drugs and their Synonyms: (An International Survey). 7th ed. (1994), Akademie Verlag GmbH, Berlin
4. Milstein D., and Stille J.K. J. Am. Chem. Soc. 100 (1978) 3636
5. Espinet P., and Echavarren A.M. Angew. Chem., Int. Ed. 43 (2004) 4704
6. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
7. Hassan J., Sévignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359
8. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400
9. Shoji T., Kikuchi S., Ito S., and Morita N. Heterocycles 66 (2005) 91
10. Ito S., Yokoyama R., Okujima T., Terazono T., Kubo T., Tajiri A., Watanabe M., and Morita N. Org. Biomol. Chem. 1 (2003) 1947
11. Corey E.J., and Tian Y. Org. Lett. 7 (2005) 5535
12. Katritzky A.R., Zhang S., Kurz T., Wang M., and Steel P.J. Org. Lett. 3 (2001) 2807
13. Similar compounds were previously reported. Ueno T., Toda H., Yasunami M., and Yoshifuji M. Chem. Lett. 24 (1995) 169
14. Ueno T., Toda H., Yasunami M., and Yoshifuji M. Bull. Chem. Soc. Jpn. 69 (1996) 1645
15. Wang D., and Imafuku K. J. Heterocycl. Chem. 37 (2000) 1019
16. Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC no. 615972 for compound 13a. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 IEZ, UK (Fax: +44-1223-336033, e-mail: deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk).
17. 1 = 0.047.
18. Toscano R.A., Rosas R., Hernandez-Galindo M.d.C., Alvarez-Toledano C., and Garcia-Mellado O. Transition Met. Chem. 23 (1998) 113
19. Bergman J., Renström L., and Sjöberg B. Tetrahedron 36 (1980) 2505
20. Zeller K.P. Azulene. 4th ed. Houben-Weyl Methoden der Organischen Chemie Vol. V, Part 2C (1985), Georg Thieme, Stuttgart p. 130
21. 2 (10 mL). The resulting solution was stirred for 30 min-2 h at room temperature and the solvent was removed in vacuo and the reaction mixture was purified by column chromatography on silica gel to give the corresponding dihydroheteroarylazulenes.
22. General procedure for the synthesis of heteroarylazulenes: 3 equiv of KOH or tert-BuOK was added to a solution of dihydroheteroarylazulenes in EtOH or DMSO. The resulting solution was stirred at room temperature for 10 min or 2 h. After a usual workup, the crude product was purified by reversed-phase chromatography (ODS/70% aq MeOH) and preparative GPC to give heteroarylazulenes.