Michael Addition of Aryl Thiols to 3-(2,2,2-Trifluoroethylidene)Oxindoles under Catalyst-Free Conditions: The Rapid Synthesis of Sulfur-Containing Oxindole Derivatives
Free accessResearch articleFirst published online April, 2018
Michael Addition of Aryl Thiols to 3-(2,2,2-Trifluoroethylidene)Oxindoles under Catalyst-Free Conditions: The Rapid Synthesis of Sulfur-Containing Oxindole Derivatives
A mild and efficient catalyst-free method for the rapid synthesis at room temperature of 3-thiomethylated oxindole derivatives has been achieved via the Michael addition of aryl thiols to ring and 1-substituted 3-(2,2,2-trifluoroethylidene)oxindoles in dichloromethane. The method was applicable to a wide range of thiols and variously substituted 3-(2,2,2-trifluoroethylidene)oxindoles under mild conditions as demonstrated by the synthesis in high yields with good diastereoselectivities of 30 3-thiomethylated oxindoles bearing a trifluoromethyl group.
NudelmanA., The chemistry of optically active sulfur compounds, ed. NudelmanA.. Gordon and Breach, New York, 1984, Vol. 9, pp. 1–79.
2.
DamaniL.A., Sulphur-containing drugs and related organic compounds, ed. DamaniL.A.. Wiley, New York, 1989, Vol. 2.
3.
da SilvaJ.R.F., and WilliamsR.J.P., The biological chemistry of the elements, eds da SilvaJ.J.R.F., and WilliamsR.J.P.. Oxford University Press, New York, 2001, Vol. 20, pp. 62–63.
4.
ChauhanP., MahajanS., and EndersD., Chem. Rev., 2014, 114, 8807.
5.
OjimaI., Fluorine in medicinal chemistry and chemical biology, ed. OIjimaI.. Wiley-Blackwell, Oxford, 2009, Vol. 22, pp. 3–16.
6.
KirschP., Modern fluoroorganic chemistry, ed. KirschP.. Wiley-VCH, Weinheim, 2004.
7.
PrakashG.K.S., WangF., O'HaganD., HuJ., DingK., and DaiL.-X., Organic chemistry: breakthroughs and perspectives, eds DingK., and DaiL.-X.. Wiley-VCH, Weinheim, 2012, pp. 413–476.
8.
YangX.-Y., WuT., PhippsR.-J., and TosteF.-D., Chem. Rev., 2015, 115, 826.
9.
ValeroG., CompanyoX., and RiosR., Chem. Eur. J., 2011, 17, 2018.
10.
ShibataN., MizutaS., and KawaiH., Tetrahedron Asymmetry, 2008, 19, 2633.
11.
MaJ.-A., and CahardD., Chem. Rev., 2008, 108, 1.
12.
NieJ., GuoH.-C., CahardD., and MaJ.-A., Chem. Rev., 2011, 111, 455.
13.
MikamiK., ItohY., and YamanakaM., Chem. Rev., 2004, 104, 1.
14.
GaoJ.-R., WuH., XiangB., YuW.-B., HanL., and JiaY.-X., J. Am. Chem. Soc., 2013, 135, 2983.