Abstract
Herein, we report a simple and metal-free protocol for the synthesis of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinolines. The present method under mild reaction conditions with wide functional group compatibility gives several unexplored N-substituted/unsubstituted 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinolines and marinoquinolines in good to excellent yields. Mechanistic insights for the synthesis of N-substituted pyrroloquinolines reveal the ring expansion of 3-ylideneoxindoles and H-shift as the key steps.
Highlights
Functionalized heteroarenes, azaheteroarenes are indispensable structural units in a large number of natural products, pharmaceuticals, agrochemicals, and functional materials.1a–e The fused azaheteroarenes such as pyrrolo[2,3-c]quinoline derivatives occupy an essential role, due to their wider occurrence in the pharmaceutically active compounds
We report the study on development of an effective method for the synthesis of N-unsubstituted as well as Nsubstituted pyrrolo[2,3-c]quinoline, which was attempted by Ji et al, but it is applicable only for the synthesis of N-unsubstituted pyrrolo[2,3-c]quinolines.[10]
The synthesis of N-substituted pyrrolo[2,3-c]quinolines are notfeasible with this strategy as N–H cleavage is involved in the isocyanate intermediate formation
Summary
Functionalized heteroarenes, azaheteroarenes are indispensable structural units in a large number of natural products, pharmaceuticals, agrochemicals, and functional materials.1a–e The fused azaheteroarenes such as pyrrolo[2,3-c]quinoline derivatives occupy an essential role, due to their wider occurrence in the pharmaceutically active compounds. These are very well explored in the literature for various medicinal applications such as a caspase 3-inhibitor,2 5HT4R antagonist,[3] ATPase inhibitor,[4] apildiopsamine,[5] and marinoquinoline A, E, and F.6. The crucial steps and offers both N-substituted and unsubstituted pyrrolo[2,3-c]quinolines
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