Hypervalent Iodine in Synthesis 73: A New Stereoselective Synthesis of 1-(1-alkenyl) Benzotriazoles by the reaction of Alkenyl(phenyl)iodonium Salts with Benzotriazole †
We report the preparation of 1-(1-alkenyl)benzotriazoles from alkenyl (phenyl)iodonium salts and benzotriazole. The reaction offers a simple and convenient route for the stereoselective synthesis of 1-(1-alkenyl)benzotriazoles. In addition, present method is particularly efficient for preparing 1-(1-alkenyl)benzotriazoles with amino-, acyl- and alkoxycarbonyl substituents, which were difficult to prepare by conventional methods.
OkuyamaT., TakinoT., SuedaT. and OchiaiM., J. Am. Chem. Soc., 1995, 117, 3360;
20.
StangP.J. and ZhdankinV.V., Chem. Rev., 1996, 96, 1123;
21.
YanJ. and ChenZ.-C., Tetrahedron Lett., 1999, 40, 5757;
22.
YanJ. and ChenZ.-C., Synth. Commun., 1999, 29, 2867;
23.
YanJ. and ChenZ.-C., Synth. Commun., 1999, 29, 3275;
24.
YanJ. and ChenZ.-C., Synth. Commun., 1999, 29, 3605;
25.
YanJ. and ChenZ.-C., Synth. Commun., 2000, 30, 1009;
26.
YanJ. and ChenZ.-C., Synth. Commun., 2000, 30, 2359;
27.
YanJ.; ChenZ.-C.Synth. Commun., 2000, 30, 3897.
28.
OchiaiM., ShuT., NagaokaT. and KitagawaY., J. Org. Chem., 1997, 62, 2130.
29.
(a)OchiaiM., OshimaK. and MasakiY., Tetrahedron Lett., 1991, 32, 7711;
30.
OchiaiM., OshimaK. and MasakiY., J. Am. Chem. Soc., 1991, 113, 7059.
31.
It was reported that for 1-(1-propenyl)benzotriazole the coupling constants of vinylic protons are 14.5Hz for the trans-isomer and 8.5Hz for the cis-isomer, see Ref.10.
32.
PapoutsisI., SpyroudisS. and VarvoglisA., Tetrahedron, 1998, 54, 1005.
33.
SHELXS86: SheldrickG. M., KrugerC. and GoddardR, (1985). In: Crystallographic Computing 3Oxford University Press, pp. 175–189.
34.
DIRDIF92: BeurskensP.T., AdmiraalG., BeurskensG., BosmanW.P., Garcia-GrandaS., GouldR.O., SmitsJ.M.M. and SmykallaC., (1992). The DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands.
35.
OaeS. and UchidaY., Acc. Chem. Res., 1991, 24, 202.