Reaction of 1-Phenacylidene pyrrolo[3,2,1-ij]quinolin-2-ones with Cyclic/Acyclic Enaminones and the Anticoagulant Activity of Synthesized Pyrrole-Quinoline Derivatives

A convenient strategy for the synthesis of pyrroles lineary linked to 4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ones is presented. The cyclization of (E)-1-(2-oxo-2-phenylethylidene)-4H-pyrrolo[3,2,1-ij]quinolin-2-ones with linear and cyclic enaminones proceeds both in the presence of p-toluenesulfonic acid and triethylamine. The obtained compounds are characterised by atropoisomerism and keto-enol tautomerism. The synthesized 1-(2-phenyl-1H-pyrrol-3-y1)-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ones were studied for anticoagulant activity.

Automated summary

A convenient strategy for the synthesis of pyrroles lineary linked to 4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ones is presented. The cyclization of (E)-1-(2-oxo-2-phenylethylidene)-4H-pyrrolo[3,2,1-ij]quinolin-2-ones with linear and cyclic enaminones proceeds both in the presence of p-toluenesulfonic acid and triethylamine. The obtained compounds are characterised by atropoisomerism and keto-enol tautomerism. The synthesized 1-(2-phenyl-1H-pyrrol-3-y1)-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ones were studied for anticoagulant activity.