Economical and environmentally friendly syntheses of three 3,4-dihydro-1H-quinoxalin-2-ones and six 1H-quinolin-2-ones have been developed by a 1: 1 reaction of o-, m-, or p-phenylenediamine with dialkyl acetylenedicarboxylates under solvent-free conditions. Some of the products were antibacterial towards both Gram positive and Gram negative microorganisms.
AnniyappanM., MuralidhranD., and PerumalP.T., Tetrahedron Lett., 2003, 44, 3653.
13.
DellA., WilliamD.H., MorrisH.R., SmithG.A., FeeneyJ., and RobertsG.C.K., J. Am. Chem. Soc., 1975, 97, 2497.
14.
HeraviM.M., BakhtiariK., TehraniM.H., JavadiN.M., and OskooieH.A., ARKIVOC, 2006, (xvi), 16.
15.
RawS.A., WilfredC.D., and TaylorR.J.K., Chem. Commun., 2003, 18, 2286.
16.
NCCLS, Methods for dilution antimicrobial susceptibility tests for bacteria which grow aerobically, 5th edn, Approved Standard M7-A5, NCCLS, Villanova, 2000.