Synthesis of N -aryl( alkyl) -9 -phenyl-pyrrolo[3,4 -b] quinoline -1 -one derivatives
ZHANG Hong
LI Yang
GAO Wen-tao
Abstract：Pyrrolo[3,4-b] quinoline-1-ones represent an important class of heterocycles and have been claimed to exhibite potent antitumor and acetylcholinesterase inhibitory activities .The reported synthetic methods have some disadvantages such as the use of toxic and harmful solvent and catalyst and tedious workup .As such, we present hevein a facile and efficient catalyst -free protocol for the synthesis of a series of pyrrolo [3,4-b] quinoline-1-ones, namely N-aryl(alkyl)-9-phenyl-2,3-dihydro -1H-pyrrolo[3,4-b]quinoline-1-ones 3 a-l has been achieved via a two -step procedure , involving a cascade Williamson -type condensation reaction of ethyl 2-( chloromethyl )-4-phenylquinoline-3-carboxylate (1) with various amines 2a-l and subsequent intramolecular C -N bond cyclization of the resulting intermediates in refluxing EtOH -AcOH ( V/V, 10:1) solvent system in a single synthetic operation .The structures of all the newly -synthesized compounds were characterized by IR , 1 H NMR, 13 C NMR and HRMS .
Keywords：quinolineaminepyrrolo[34 -b] quinoline -1-oneWilliamson reactionintramolecular cyclization
Publication Date：2017-01-01
Online Publishing Date：2025-08-15(First online date of this platform, not the publication date of the document)
Pages：8( 248-255 )