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 2009(11): 1797-1800
DOI: 10.1055/s-0028-1088078
DOI: 10.1055/s-0028-1088078
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkA Facile and Practical One-Pot Synthesis of β-Oxo Thioamides from β-Oxo Amides and Isothiocyanates
Weitere Informationen
Received
24 December 2008
Publikationsdatum:
27. April 2009 (online)
Publikationsverlauf
Publikationsdatum:
27. April 2009 (online)

Abstract
A facile and practical one-pot synthesis of β-oxo thioamides from β-oxo amides has been developed. By treatment with isothiocyanates in ethanol in the presence of potassium carbonate, a series of β-oxo amides was converted, under reflux, in high yields into the corresponding β-oxo thioamides.
Key words
thioamides - 3-oxo amides - isothiocyanates - ethanol - potassium carbonate
- 1a
Bauer W.Kühlein K. In Houben-Weyl Vol. E5:Falbe J. Thieme; Stuttgart: 1985. p.1218-1279 - 1b
Schaumann E. In Comprehensive Organic Synthesis Vol. 6:Trost BM.Fleming I. Pergamon; Oxford: 1991. p.419-434 - For reviews on the synthesis and applications of thioamides, see:
- 2a
Hurd RN.Delamater G. Chem. Rev. 1961, 61: 45 - 2b
Walter W.Bode K.-D. Angew. Chem., Int. Ed. Engl. 1966, 5: 447 - 2c
Takahata H.Yamazaki T. Heterocycles 1988, 27: 1953 - 2d
Jagodzinski TS. Chem. Rev. 2003, 103: 197 - For selected examples, see:
- 3a
Kolakowski RV.Shangguan N.Williams LJ. Tetrahedron Lett. 2006, 47: 1163 - 3b
Varma RS.Kumar D. Org. Lett. 1999, 1: 697 - 3c
Zbruyev OI.Stiasni N.Kappe CO. J. Comb. Chem. 2003, 5: 145 - 3d
Brain CT.Hallett A.Ko SY. J. Org. Chem. 1997, 62: 3808 - 3e
Charette AB.Grenon M. J. Org. Chem. 2003, 68: 5792 - 3f
Pfund E.Masson S.Vazeux M.Lequeux T. J. Org. Chem. 2004, 69: 4670 - 3g
Kaleta Z.Makowski BT.Soos T.Dembinski R. Org. Lett. 2006, 8: 1625 - 3h
Kaboudin B.Elhamifar D. Synthesis 2006, 224 - 4
Brillon D. Sulfur Rep. 1992, 12: 297 - 5a
Scheeren JW.Ooms PHJ.Nivard RJF. Synthesis 1973, 149 - 5b
Dash B.Dora EK.Panda CS. Heterocycles 1982, 19: 2093 - 5c
Cava MP.Levinson MI. Tetrahedron 1985, 41: 5061 - 5d
Jones BA.Bradshaw JS. Chem. Rev. 1984, 84: 17 - 6a
Hartke K.Gerber H.-D. J. Prakt. Chem. 1996, 338: 763 - 6b
Raucher S.Klein P. J. Org. Chem. 1981, 46: 3558 - 6c
Brillon D. Synth. Commun. 1990, 20: 3085 - 6d
Goel OP.Krolls U. Synthesis 1987, 162 - 6e
Curphey TJ. J. Org. Chem. 2002, 67: 6461 - 7a
Ogata M.Matsumoto H. Heterocycles 1978, 11: 139 - 7b
Hirabayashi T.Inoue K.Yokota K. J. Organomet. Chem. 1975, 92: 139 - 7c
Steliou K.Mrani M. J. Am. Chem. Soc. 1982, 104: 3104 - 7d
Wojtkowski PW.Dolfini JE.Kocy O.Cimarusti CM. J. Am. Chem. Soc. 1975, 97: 5628 - 8a
Ilankumaran P.Ramesha AR.Chandrasekaran S. Tetrahedron Lett. 1995, 36: 8311 - 8b
Smith DC.Lee SW.Fuchs PL. J. Org. Chem. 1994, 59: 348 - 8c
Bodine JJ.Kaloustian M. Synth. Commun. 1982, 12: 787 - 9
Ley SV.Leach AG.Storer RI. J. Chem. Soc., Perkin Trans. 1 2001, 358 - 10a
Jagodziński T. Synthesis 1988, 717 - 10b
Jagodziński T. Org. Prep. Proced. Int. 1990, 22: 755 - 10c
Jagodziński T.Jagodzińska E.Jaboński Z. Tetrahedron 1986, 42: 3683 - 11
Liang F.Li Y.Li D.Cheng X.Liu Q. Tetrahedron Lett. 2007, 48: 7938 - For reviews on the synthesis and applications of α-oxo ketene S,S-acetals, see:
- 12a
Dieter RK. Tetrahedron 1986, 42: 3029 - 12b
Junjappa H.Ila H.Asokan CV. Tetrahedron 1990, 46: 5423 - 12c
Kolb M. Synthesis 1990, 171 - 13a
Dong D.Ouyang Y.Yu H.Liu Q.Liu J.Wang M.Zhu J. J. Org. Chem. 2005, 70: 4535 - 13b
Liu Q.Che G.Yu H.Liu Y.Zhang J.Zhang Q.Dong D. J. Org. Chem. 2003, 68: 9148 - 13c
Yu H.Liu Q.Yin Y.Fang Q.Zhang J.Dong D. Synlett 2004, 999 - 13d
Sun R.Liu Q.Yu H.Zhao Y.Liu J.Ouyang Y.Dong D. Chin. J. Chem. 2005, 23: 1060 - 14a
Barnikow G. J. Prakt. Chem. 1966, 34: 251 - 14b
Zankowska-Jasińska W.Gauszka B. J. Fluorine Chem. 1983, 22: 165 - 15a
Foye WO. J. Chem. Ed. 1969, 46: 841 - 15b
Larsson FCV.Lawesson SO. Tetrahedron 1972, 28: 5341