A direct synthetic protocol is developed for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via a three-component condensation of primary amines, triethyl orthoformate and sodium azide in the presence of 5 mol% of trifluoromethanesulfonimide (HNTf2) in glycerol at room temperature with good to excellent yields.
GeninM.J., AllwineD. A., AndersonD. J., BarbachynM. R., EmmertD. E., GarmonS. A., GraberD. R., GregaK. C., HesterJ. S., HutchinsonD. K., MorrisJ., ReischerR. J., FordC. W., ZurenkoG. E., HamelJ. C., SchaadtR. D., StapertD., and YagiB. H., J. Med. Chem., 2000, 43, 953.
2.
WardP., ArmourD. R., BaysD. E., EvansB., GiblinG. M. P., HernonN., HubbardT., LiangK., MiddlemissD., MordauntJ., NaylorA., PeggN. A., VinaderM. V., WatsonS. P., BountraC., and EvansD. C., J. Med. Chem., 1995, 38, 4985.
3.
SinghR.P., VermaR. D., MeshriD. T., and ShreeveJ. M., Angew. Chem. Int. Ed., 2006, 45, 3584.
4.
SteinhauserG., and KlapotkeT. M., Angew. Chem. Int. Ed., 2008, 47, 3330.
5.
SinghH., ChawlaA. S., KapoorV. K., PaulD., and MalhotraR. K., Prog. Med. Chem., 1980, 17, 151.
6.
FallonF.G., and HerbstR. M., J. Org. Chem., 1957, 22, 933.
7.
JinT., KamijoS., and YamamotoY., Tetrahedron Lett., 2004, 45, 9435.
8.
SatohY., and MarcopulosN., Tetrahedron Lett., 1995, 36, 1759.
9.
KunduD., MajeeA., and HajraA., Tetrahedron Lett., 2009, 50, 2668.
10.
SuW.K., HongZ., ShanW. G., and ZhangX. X., Eur. J. Org. Chem., 2006, 2723.
11.
PotewarT.M., SiddiquiS. A., LahotiR. J., and SrinivasanK. V., Tetrahedron Lett., 2007, 48, 1721.
