RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2007(23): 3653-3658
DOI: 10.1055/s-2007-990865
DOI: 10.1055/s-2007-990865
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Bis- and Trisoxazole Derivatives via Suzuki-Miyaura Cross-Coupling Reaction and van Leusen Oxazole Synthesis
Weitere Informationen
Received
20 August 2007
Publikationsdatum:
31. Oktober 2007 (online)
Publikationsverlauf
Publikationsdatum:
31. Oktober 2007 (online)
Abstract
Both C 2- and C 3-symmetric oxazole derivatives are synthesized via the Suzuki-Miyaura cross-coupling and van Leusen oxazole synthesis. Here, bis- and triscarboxaldehydes were obtained via the Suzuki-Miyaura cross-coupling and further treated with p-toluenesulfonylmethyl isocyanide (TosMIC) in the presence of potassium carbonate as a base and methanol as a solvent to deliver the corresponding oxazole derivatives.
Key words
bisoxazole - Suzuki-Miyaura cross-coupling - trisoxazole - TosMIC
- 1
Brown DJ. Chemistry of Heterocyclic Compounds, Oxazoles: Synthesis, Reactions and SpectroscopyPalmer D. C. Vol. 60: Wiley-Interscience; Hoboken NJ: 2003. Part A. p.1-390 - 2
Axelrod B.Belzile JR. J. Org. Chem. 1958, 23: 919 - 3
Crow WD.Hodgkin JH. Tetrahedron Lett. 1963, 4: 85 - 4
Joshi BS.Taylor WI.Bhate DS.Karmkar SS. Tetrahedron 1963, 16: 1437 - 5
Koyama Y.Yokose K.Dolby LJ. Agric. Biol. Chem. 1981, 45: 1285 - 6
Dominguez XA.de la Fuente G.Gonzalez AG.Reina M.Timon I. Heterocycles 1988, 27: 35 - 7
Sintchak MD.Nimmesgern E. Immunopharmacology 2000, 47: 163 - 8
Henkel T.Zeeck A. Liebgis Ann. Chem. 1991, 367 - 9
Shiomi K.Arai N.Shinose M.Takahashi Y.Yoshida H.Iwabuchi J.Tanaka Y.Omura S. J. Antibiot. 1995, 48: 714 - 10
Brossi A.Wenis E. J. Heterocycl. Chem. 1965, 2: 310 - 11
Takeuchi H.Yanagida S.Ozaki T.Haiwara S.Eguchi S. J. Org. Chem. 1989, 54: 431 - 12
Molina P.Fressneda PM.Almendros P. Heterocycles 1993, 36: 2255 -
13a
Gabriel S. Ber. Dtsch. Chem. Ges. 1910, 43: 1283 -
13b
Robinson R. J. Chem. Soc. 1909, 95: 2167 -
14a
Schöllkopf U.Gerhart E. Angew. Chem., Int. Ed. Engl. 1968, 7: 805 -
14b
Schöllkopf U.Schröder R. Angew. Chem., Int. Ed. Engl. 1971, 10: 333 -
15a
Haung W.-S.Zhang Y.-X.Yaun C.-Y. Synth. Commun. 1996, 26: 1149 -
15b
Bossio R.Marcaccini S.Pepino R. Heterocycles 1986, 24: 2003 -
15c
Ozaki Y.Maeda S.Iwasaki T.Matsumoto K.Odawara A.Sasaki Y.Morita T. Chem. Pharm. Bull. 1983, 12: 4417 -
15d
Ohba M.Kubo H.Seto S.Fujii T.Ishibashi H. Chem. Pharm. Bull. 1998, 46: 860 -
15e
Tang J.Varkade JG. J. Org. Chem. 1994, 59: 7793 - 16
van Leusen AM.Hoogenboom BE.Siderius H. Tetrahedron Lett. 1972, 23: 2369 - 17
Sasaki H.Kitagawa T. Chem. Pharm. Bull. 1988, 36: 1593 - 18
Atkins JM.Vedejs E. Org. Lett. 2005, 15: 3351 - 19
Kulkarni BA.Ganesan A. Tetrahedron Lett. 1999, 40: 5633 - 20
Kulkarni BA.Ganesan A. Tetrahedron Lett. 1999, 40: 5637 - 21
Barrett AGM.Cramp SM.Hennessy AJ.Procopiou PA.Roberts RS. Org. Lett. 2001, 3: 271 -
22a
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
22b
Kotha S.Lahiri K.Kashinath D. Tetrahedron 2002, 58: 9633 -
22c
Kotha S.Lahiri K. Eur. J. Org. Chem. 2007, 1221 -
23a
Kotha S.Kashinath D.Lahiri K.Sunoj RB. Eur. J. Org. Chem. 2004, 4003 -
23b
Kotha S.Chakraborty K.Brahmachary E. Synlett 1999, 1621 - 24
Weber E.Hecker M.Koeep E.Orlia W.Czuglar M.Csöregh I. J. Chem. Soc., Perkin Trans. 2 1988, 1251 - 25
Reger DL.Watson RP.Smith MD.Pellechia PJ. Organometallics 2006, 25: 743 - 26
Murdock KC.Child RG.Lin Y.Warren JD.Fabio PF.Lee VJ.Izzo PT.Lang SA.Angier RB.Citarella RV.Wallace RE.Durr FE. J. Med. Chem. 1982, 25: 505 - 27
Rajakumar P.Swaroop MG.Jayavelu S.Murugesan K. Tetrahedron 2006, 62: 12041 - 28
Kozáková M.Buděšínsky M.Hodačová J. Synth. Commun. 2005, 35: 161