Synthesis of New Polyheterocyclic Compounds Based on Chalcones

Abstract

The reaction of methyl N-{4-[2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetyl]phenyl}carbamate with tosylmethyl isocyanide in tetrahydrofuran in the presence of potassium tert-butoxide led to the formation of methyl N-{4-[(4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinolin-1-yl)carbonyl]phenyl}carbamate. Three-component condensation of methyl N-{4-[(E)-3-R-prop-2-enoyl]phenyl}carbamates and methyl N-{4-[2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetyl]phenyl}carbamate with sarcosine and paraformaldehyde in boiling toluene with simultaneous removal of water by azeotropic distillation afforded methyl N-(4-{4-[4-R-1-methyl-pyrrolidin-3-yl]carbonyl}phenyl)carbamates and methyl N-[4-(1′-methyl-2-oxo-1,2-dihydrospiro[indole-3,3′-pyrrolidin]-4′-ylcarbonyl)phenyl]carbamate, respectively.