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Synthesis 2009(11): 1797-1800
DOI: 10.1055/s-0028-1088078
DOI: 10.1055/s-0028-1088078
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Facile and Practical One-Pot Synthesis of β-Oxo Thioamides from β-Oxo Amides and Isothiocyanates
Further Information
Received
24 December 2008
Publication Date:
27 April 2009 (online)
Publication History
Publication Date:
27 April 2009 (online)
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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