Free accessResearch articleFirst published online 2016-2
A Practical Approach for the Synthesis of Novel Triazolo-fused Benzazepine Derivatives Using a Multi-component Reaction and an Intramolecular C–H Arylation
An efficient and straightforward method has been developed for the preparation of triazolo-fused benzazepines by a facile, one-pot Ugi multi-component reaction/click reaction. In this strategy, the Ugi-reaction products were coupled by a click reaction, thus integrating the triazole fragment into the benzazepine structure using an intramolecular C–H arylation. The corresponding products were obtained in good yields without unfavourable by-products.
KostyrkoE.O., KovtunenkoV. A., and KysilV. M., Chem Heterocycl Compd., 2006, 42, 886.
2.
WeinstockJ., LaddD. L., WilsonJ. W., BrushC. K., YimN. C., GallagherG.Jr., McCarthyM.E., SilvestriJ., and SarauH.M., J. Med. Chem., 1986, 29, 2315.
3.
YuL.T., HuangJ.-L., ChangC.-Y., and YangT.-K., Molecules, 2006, 11, 641.
4.
WeinstockJ., LaddD. L., WilsonJ. W., BrushC. K., YimN. C., GallagherG.Jr., McCarthyM. E., SilvestriJ., and SarauH.M., J. Med. Chem., 1986, 29, 2315.
5.
SmithB.M., SmithJ. M., TsaiJ. H., SchultzJ. A., GilsonC. A., EstradaS. A., ChenR. R., ParkD. M., PrietoE. B., and GallardoC. S., J. Med. Chem., 2008, 51, 305.
6.
PasikantiS., SrinivasaR. D., VenkateshamB., DubeyP., IqbalJ., and DasP., Tetrahedron Lett., 2012, 51, 151.
7.
PrasadJ.V., PrabhakarM., ManjulathaK., RambabuD., SolomonK. A., KrishnaG. G., and KumarK. A., Tetrahedron Lett., 2010, 51, 3109.
8.
BuckleD.R., RockellC. J. M., SmithH., and SpicerB. A., J. Med. Chem., 1986, 29, 2262.
9.
GeninM.J., AllwineD. A., AndersonD. J., BarbachynM. R., EmmertD. E., GarmonS. A., GraberD. R., GregaK. C., HesterJ. B., HutchinsonD. K., MorrisJ., ReischerR. J., FordC. W., ZurenkoG. E., HamelJ. C., SchaadtR. D., StapertD., and YagiB. H., J. Med. Chem., 2000, 43, 953.
10.
AlvarezR., VelazquezS., San-FelixA., AquaroS., ClercqE. D., PernoC.-F., KarlssonA., BalzariniJ., and CamarasaM. J., J. Med. Chem., 1994, 37, 4185.
11.
JordãoA.K., FerreiraV. F., LimaE. S., de SouzaM. C. B. V., CarlosE. C. L., CastroH. C., GeraldoR. B., RodriguesC. R., AlmeidaM. C. B., and CunhaA. C., Bioorg. Med. Chem., 2009, 17, 3713.
12.
ChengH., WanJ., LinM.-I., LiuY., LuX., LiuJ., XuY., ChenJ., TuZ., ChengY.-S. E., and DingK., J. Med. Chem., 2012, 55, 2144.
13.
BoechatN., FerreiraV. F., FerreiraS. B., FerreiraM. de L. G., da SilvaF. de C., BastosM. M., CostaM. dos S., LourençoM. C. S., PintoA. C., KrettliA. U., AguiarA. C., TeixeiraB. M., da SilvaN. V., MartinsP. R. C., BezerraF. A. F. M., CamiloA. L. S., da SilvaG. P., and CostaC. C. P., J. Med. Chem., 2011, 54, 5988.