A simple and convenient method for one-pot synthesis of a series of potentially biologically active [1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide derivatives has been developed in solvent-free conditions using maltose as a commercially available, cheap and eco-friendly catalyst. The salient features of the present protocol are mild reaction conditions, good to excellent yields, high atom economy, benign environmental conditions, easy isolation of products without column chromatography and clean reaction profiles.
VuC.B., ShieldsP., PengB., KumaravelG., JinX. W., PhadkeD., WangJ., EngberT., AyyubE., and PetterR. C., Bioorg. Med. Chem. Lett., 2004, 14, 4835.
12.
JacksonR., GhoshD., and PatersonG., Pest. Manag. Sci., 2000, 56, 1065.
13.
GeinV.L., ZamaraevaT. M., and VakhrinM. I., Russ. J. Gen. Chem., 2014, 84, 82.
14.
SatoY., ShimojiY., FujitaH., NishinoH., MizunoH., KobayashiS., and KumakuraS., J. Med. Chem., 1980, 23, 927.
15.
Abdel-RahmanH.M., El-KoussiN. A., and HassanH. Y., Arch. Pharm. Chem. Life. Sci., 2009, 342, 94.
16.
IvachtchenkoA.V., GolovinaE. S., KadievaM. G., KoryakovaA. G., KovalenkoS. M., MitkinO. D., OkunI. M., RavnyeykoI. M., TkachenkoS. E., and ZarembaO. V., Bioorg. Med. Chem., 2010, 18, 5282.
17.
NovinsonT., SpringerR. H., O'BrienD. E., ScholtenM. B., MillerJ. P., and RobinsR. K., J. Med. Chem., 1982, 25, 420.
18.
KleschickW.A., CostalesM. J., DunbarJ. E., MeikleR. W., MonteW. T., PearsonN. R., SniderS. W., and VinogradoffA. P., Pest. Manag. Sci., 1990, 29, 341.
19.
ChenQ., ZhuX. L., JiangL. L., LiuZ. M., and YangG. F., Eur. J. Med. Chem., 2008, 43, 595.
20.
SaidS.A., AmrA. E. G., SabryN. M., and AbdallaM. M., Eur. J. Med. Chem., 2009, 44, 4787.
21.
ZhangN., KaloustianS., NguyenT., AfragolaJ., HernandeR., LucasJ., GibbonsJ., and BeyerC., J. Med. Chem., 2007, 50, 319.
22.
ChandrasekharS., JohnyK., and ReddyC. R., Tetrahedron Asymmetry, 2009, 20, 1742.
23.
Khalafi-NezhadA., ParhamiA., ZareA., Moosavi-ZareA. R., HasaninejadA., and PanahiF., Synthesis, 2008, 4, 617.
24.
DekaminM.G., Sagheb-AslS., and Naimi-JamalM. R., Tetrahedron Lett., 2009, 50, 4063.
MousaviM.R., HazeriN., MaghsoodlouM. T., SalahiS., and Habibi-KhorassaniS. M., Chin. Chem. Lett., 2013, 24, 411.
27.
LashkariM., MaghsoodlouM. T., HazeriN., Habibi-KhorassaniS. M., SajadikhahS. S., and DoostmohamadiR., Synth. Commun., 2013, 43, 635.
28.
WangH., LeeM., PengZ., BlázquezB., LastochkinE., KumarasiriM., BouleyR., ChangM., and MobasheryS., J. Med. Chem., 2015, 58, 4194.
29.
TkachenkoV.V., MuravyovaE. A., DesenkoS. M., ShishkinO. V., ShishkinaS. V., SysoievD. O., MüllerT. J. J., and ChebanovV. A., Beilstein J. Org. Chem., 2014, 10, 3019.