An efficient one-pot palladium- and copper-free procedure has been developed for a convenient synthesis of 3,5 -disubstituted-1H-pyrazoles from various acid chlorides, terminal alkynes and hydrazine by a coupling reaction and cyclocondensation sequence. Acid chlorides react with terminal alkynes in the presence of silica-supported-zinc bromide to give α,β-unsaturated ynones, and in situ conversion into pyrazoles by the hydrazine cyclocondensation.
GomezL., HackM. D., WuJ., WienerJ. J. M., VenkatesanH. A. S., PippelD. J., ManiN., MorrowB. J., MotleyS. T., ShawK. J., WolinR., GriceC. A., and JonesT. K., Bioorg Med Chem Lett., 2007, 17, 2723.
PintoD. J. P., OrwatM. J., KochS., RossiK. A., AlexanderR. S., SmallwoodA., WongP. C., RendinaA. R., LuettgenJ. M., KnabbR. M., HeK., XinB., WexlerR. R., and LamP. Y. S., J. Med. Chem., 2007, 50, 5339.
6.
GhotekarB. K., GhagareM. G., TocheR. B., and JachakM. N., Monatsh. Chem., 2010, 141, 169.
7.
ChimentiF., BolascoA., MannaF., SecciD., ChimentiP., GraneseA., BefaniO., TuriniP., AlcaroS., and OrtusoF., Chem Biol Drug Des, 2006, 67, 206.
8.
LinR., ChiuG., YuY., ConnollyP. J., LiS. J., LuY. H., AdamsM., Fuentes-PesqueraA. R., EmanuelS. L., and GreenbergerL. M., Bioorg Med Chem Lett., 2007, 17, 4557.
9.
PenningT. D., TalleyJ. J., BertenshawS. R., CarterJ. S., CollinsP. W., DocterS., GranetoM. J., LeeL. F., MalechaJ. W., MiyashiroJ. M., RogersR. S., RogierD. J., YuS. S., AndersonG. D., BurtonE. G., CogburnJ. N., GregoryS. A., KoboldtC. M., PerkinsW. E., SeibertK., VeenhuizenA. W., ZhangY. Y., and IsaksonP. C., J. Med. Chem., 1997, 40, 1347.
10.
ElgueroJ., GoyaP., JagerovicN., and SilvaA. M. S. (2002) Targets in heterocyclic systems—chemistry and propertiesAttanasiO.A., and SpinelliD. (eds). Italian Society of Chemistry, Rome, vol 6, p. 52.
11.
ZhuL., ChengL., ZhangY., XieR., and YouJ., J. Org. Chem., 2007, 72, 2737.
12.
BurlingS., FieldL. D., MesserleB. A., and RumbleS. L., Organometallics, 2007, 26, 4335.
13.
MartinsM. A. P., PeresR. L., FrizzoC. P., ScapinE., MoreiraD. N., FissG. F., ZanattaN., and BonacorsoH. G., J. Heterocycl. Chem., 2009, 46, 1247.
14.
ReidlingerC., DworczakR., and JunekH., Monatsh. Chem., 1998, 129, 1207.
15.
SilvaV. L. M., SilvaA. M. S., PintoD. C. G. A., JagerovicN., CalladoL. F., CavaleiroJ. A. S., and ElgueroJ., Monatsh. Chem., 2007, 138, 797.
16.
ChimentiF., BolascoA., MannaF., SecciD., ChimentiP., GraneseA., BefaniO., TuriniP., AlcaroS., and OrtusoF., Chem. Biol. Drug Des., 2006, 67, 206.
17.
NikpourF., and BeigvandM., Monatsh. Chem., 2008, 139, 821.
18.
MakinoK., KimH. S., and KurasawaY., J. Heterocycl. Chem., 1998, 35, 489.
19.
HellerS. T., and NatarajanS. R., Org. Lett., 2006, 8, 2675.
20.
AggarwalV. K., de VicenteJ., and BonnertR. V., J. Org. Chem., 2003, 68, 5381.
