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Synlett 2005(6): 0947-0950
DOI: 10.1055/s-2005-864805
DOI: 10.1055/s-2005-864805
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of 2(5H)-Furanones via Oxidative Ring Expansion of 4-Hydroxy-2-cyclobutenones
Further Information
Received
26 January 2005
Publication Date:
23 March 2005 (online)
Publication History
Publication Date:
23 March 2005 (online)
Abstract
A new method to reduce cyclobutenediones towards 4-hydroxy-2-cyclobutenones was established. The latter compounds gave rise to new 5-halo-2(5H)-furanones by reaction with halogenating agents via a cationic ring-opening-ring-closure mechanism.
Key words
cyclobutenones - 2(5H)-furanones - ring expansion - rearrangements - oxidations
-
1a
Perri ST.Foland LD.Decker OHW.Moore HW. J. Org. Chem. 1986, 51: 3067 -
1b
Moore HW.Perri ST. J. Org. Chem. 1988, 53: 996 -
1c
Foland LD.Karlsson JO.Perri ST.Schwabe R.Xu SL.Patil S.Moore HW. J. Am. Chem. Soc. 1989, 111: 975 -
1d
Liebeskind LS.Iyer S.Jewell CF. J. Org. Chem. 1986, 51: 3065 -
1e
Danheiser RL.Casebier DS.Loebach JL. Tetrahedron Lett. 1992, 33: 1149 -
1f
Liebeskind LS.Foster BF. J. Am. Chem. Soc. 1990, 112: 8612 -
1g
Perri ST.Moore HW. J. Am. Chem. Soc. 1990, 112: 1897 -
1h
Gurski A.Liebeskind LS. J. Am. Chem. Soc. 1993, 115: 6101 -
1i
Lee KH.Moore HW. Tetrahedron Lett. 1993, 34: 235 -
1j
Liebeskind LS.Wang J. J. Org. Chem. 1993, 58: 3550 -
2a
Mingo P.Zhang S.Liebeskind LS. J. Org. Chem. 1999, 64: 2145 -
2b
Liebeskind LS.Wang JY. Tetrahedron 1993, 49: 5461 -
3a
Zhang S.Liebeskind LS. J. Org. Chem. 1999, 64: 4042 -
3b
Gurski-Birchler A.Liu F.Liebeskind LS. J. Org. Chem. 1994, 59: 7737 -
4a
Liebeskind LS.Chidambaram R.Mitchell D.Foster BS. Pure Appl. Chem. 1988, 60: 27 -
4b
Liebeskind LS.Bombrun A. J. Org. Chem. 1994, 59: 1149 -
4c
Yamamoto Y.Ohno M.Eguchi S. Tetrahedron Lett. 1995, 36: 5539 -
4d
Liebeskind LS.Mitchell D.Foster BS. J. Am. Chem. Soc. 1987, 109: 7908 -
5a
Ohno M.Yamamoto Y.Eguchi S. Synlett 1998, 1167 ; and references cited therein -
5b
Lee KH.Moore HW. J. Org. Chem. 1995, 60: 735 -
5c
Wang J.Jiang X.Chen M.Ge Z.Hu Y.Hu H. J. Chem. Soc., Perkin Trans. 1 2001, 66 -
5d
Ohno M.Yamamoto Y.Eguchi S. Tetrahedron Lett. 1993, 34: 4807 -
5e
Perri ST.Foland LD.Moore HW. Tetrahedron Lett. 1988, 29: 3529 -
5f
Dillon JL.Gao Q. J. Org. Chem. 1994, 59: 6868 -
6a
Yamamoto Y.Ohno M.Eguchi S. J. Org. Chem. 1994, 59: 4707 -
6b
Yamamoto Y.Ohno M.Eguchi S. J. Am. Chem. Soc. 1995, 117: 9653 -
6c
Yamamoto Y.Ohno M.Eguchi S. J. Org. Chem. 1996, 61: 9264 - 7
Ohno M.Oguri I.Eguchi S. J. Org. Chem. 1999, 64: 8995 - 8
Ohno M.Noda M.Yamamoto Y.Eguchi S. J. Org. Chem. 1999, 64: 707 -
9a
Akiyoshi Y,Tsutsumiuchi K,Narita I,Okada T,Nakamura K, andNakamura A. inventors; Jpn. Kokai Tokkyo Koho, JP 2000053670 A2 20000222. ; Chem. Abstr. 2000, 132, 166117 -
9b
Wingert H,Sauter H,Benoit R,Roehl F,Ammerman E, andLorenz G. inventors; Eur. Pat. Appl., EP 567828 A2 19931103. ; Chem. Abstr. 1993, 121, 82723 - 10
Sabatucci JP. inventors; US Patent US 5336687 A2 19940809. ; Chem. Abstr. 1994, 121, 255631 - 11
Biber A.Dienel A. Int. J. Clin. Pharm. Ther. 1996, 34: 6 ; Chem. Abstr. 1996, 124, 249586 - 12
Liu T.-X. Crop. Prot. 2004, 23: 505 -
13a
Liebeskind LS.Fengl RW.Wirtz KR.Shawe TT. J. Org. Chem. 1988, 53: 2482 -
13b
Krysan DJ.Gurski A.Liebeskind LS. J. Am. Chem. Soc. 1992, 114: 1412 -
13c
MacDougall JM.Santora VJ.Verma SK.Turnbull P.Hernandez CR.Moore HW. J. Org. Chem. 1998, 63: 6905 -
13d
Liebeskind LS.Wirtz KR. J. Org. Chem. 1990, 55: 5350 -
13e
Edwards JP.Krysan DJ.Liebeskind LS. J. Org. Chem. 1993, 58: 3942 - Cyclobutenediones 7 were synthesized according to a recently described procedure starting from 2,2-dichloro-cyclobutanones. For synthetic procedures and experimental details, see: Verniest, G.; Colpaert, J.; Törnroos, K. W.; De Kimpe, N. J. Org. Chem., submitted for publication. For other synthetic procedures, see:
-
14a
Bellus D. J. Am. Chem. Soc. 1978, 100: 8026 -
14b
Frauenrath H. In Houben-Weyl, Methoden der Organischen Chemie Vol. E15.2:Kropf H.Schaumann E. Georg Thieme Verlag; Stuttgart, New York: 1993. -
14c
de Meijere A.Kozhushkov SI.Butenschön H. In Houben-Weyl, Methods of Organic Chemistry Vol. E17f:de Meijere A. Georg Thieme Verlag; Stuttgart, New York: 1997. - 15
Campbell AC.Maidment MS.Pick JH.Stevenson DMF. J. Chem. Soc., Perkin Trans. 1 1985, 8: 1567