Free accessResearch articleFirst published online 2015-5
Solvent-Free Synthesis of Novel Benzodiazepine Derivatives by a Three-Component Base-Catalysed Reaction of Isatoic Anhydride,a Primary Amine and Chloroacetyl Chloride
Heating isatoic anhydride with a series of primary amines at 150 °C under solvent-free conditions yielded 2-amino-N-alkylbenzamides which, in the same pot, reacted readily with chloroacetyl chloride in the presence of poly(dimethylaminoethyl acrylamide)-modified magnetic nanoparticles (MNP@PDMA), a base catalyst, to give 4-alkyl-1,4-benzodiazepine-2,5-diones in good yields without formation of by-products.
SharmaO., SinglaR. K., and ShrivastavaB., Indo Glob. J. Pharm. Sci., 2012, 2, 142.
2.
CostantinoL., and BarloccoD., Curr. Med. Chem., 2006, 13, 65.
3.
RudolphU., and MöhlerH., Curr. Opin. Pharmacol., 2006, 6, 18.
4.
KoblishH. K., ZhaoS., FranksC. F., DonatelliR. R., TominovichR. M., LaFranceL. V., LeonardK. A., GushueJ. M., ParksD. J., and CalvoR. R., Mol. Cancer. Ther., 2006, 5, 160.
5.
ParksD. J., LaFranceL. V., CalvoR. R., MilkiewiczK. L., Jose MaruganJ., RaboissonP., SchubertC., KoblishH. K., ZhaoS., and FranksC. F., Bioorg. Med. Chem. Lett., 2006, 16, 3310.
6.
UrsiniA., CapelliA. M., CarrR. A., CassaraP., CorsiM., CurcurutoO., CurottoG., Dal CinM., DavalliS., and DonatiD., J. Med. Chem., 2000, 43, 3596.
7.
BlackburnB. K., LeeA., BaierM., KohlB., OliveroA. G., MatamorosR., RobargeK. D., and McDowellR. S., J. Med. Chem., 1997, 40, 717.
8.
McDowellR. S., BlackburnB. K., GadekT. R., McGeeL. R., RawsonT., ReynoldsM. E., RobargeK. D., SomersT. C., and ThorsettE. D., J. Am. Chem. Soc., 1994, 116, 5077.
9.
JosephC. G., WilsonK. R., WoodM. S., SorensonN. B., PhanD. V., XiangZ., WitekR. M., and Haskell-LuevanoC., J. Med. Chem., 2008, 51, 1423.
10.
DomlingA., Chem. Rev., 2006, 106, 17.
11.
GunawanS., AyazM., De MolinerF., FrettB., KaiserC., PatrickN., XuZ., and HulmeC., Tetrahedron, 2012, 68, 5606.
12.
DonaldJ. R., WoodR. R., and MartinS. F., ACS Combi. Sci., 2012, 14, 135.
