Free accessResearch articleFirst published online 2004-2
Organic Reactions in Ionic Liquids: A Novel Method for the Synthesis of 2-Arylthiobenzothiazoles by the S-Arylation of Benzolthiazole-2-Thiol with Diaryliodonium Salts
2-Arylthiobenzothiazoles were readily prepared in good yields by the S-arylation of benzothiazole-2-thiol with diaryliodonium salts at room-temperature in the ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4). The ionic liquid can be recycled and reused.
LarsenA.S., HolbreyJ. D., ThamF. S., and ReedC. A., J. Am. Chem. Soc., 2000, 122, 7264.
3.
Olivier-BourbigouH., and MagnaL., J. Mol. Catal. A: Chem., 2002, 182, 419.
4.
(a) GreenL., HemeonI., and SingerR. D., Tetrahedron. Lett., 2000, 41, 1343.
5.
StarkA., MacLeanB. L., and SingerR. D., J. Chem. Soc. Dalton Trans., 1999, 63.
6.
AdamsC.J., EarleM. J., and SeddonK. R., Chem. Commun., 1999, 1043.
7.
HuddlestonJ.G., WillauerH. D., SwatloskiR. P., VisserA. E., and RogersR. D., Chem. Commun., 1998, 1765.
8.
(a) ChenZ.C., JinY. Y., and StangP. J., J. Org. Chem., 1987, 52, 4115.
9.
ChenZ.C., JinY. Y., and StangP. J., J. Org. Chem., 1987, 52, 4117.
10.
ChenZ.C., JinY. Y., and YangR. Y., Synthesis., 1988, 723.
11.
YouJ.Z., and ChenZ. C., Synthesis., 1992, 521.
12.
YouJ.Z., and ChenZ. C., Synthesis., 1992, 633.
13.
LiuZ.D., and ChenZ. C., Synthesis., 1993, 373.
14.
LiuZ.D., ZengH., and ChenZ. C., Synth. Commun., 1994, 24, 475.
15.
ZhouT., and ChenZ. C., Heteroatom Chem., 2002, 13, 617.
16.
WangF.Y., ChenZ. C., and ZhengQ. G., J. Chem. Res. (S)., 2003, in press; Organic reactions in ionic liquids: ionic liquid-accelerated arylation of sodium arenesulfinates with diaryliodonium salts – an efficient method for the synthesis of diaryl sulfones.
17.
NesmeyanovA.N., MakarovaL. G., and TolstayaT. P., Tetrahedron, 1957, 145.
NesynovE.P., BesprozvannayaM. M., and Pel'kisP. S., Khim. Geterotsikl. Soedin. Sb., 1971, 3, 202; (Chem. Abstr., 1973, 78, 43364).
32.
Kotali and Varvoglis reported the thermal decomposition of iodanes (R-S-IPh2, R=benzothiazole) to give 2-phenylthiobenzothiazoles, see KotaliE., and VarvoglisA., J. Chem. Res. (S)., 1989, 142.