5-Aminopyrazole-4-carbonitriles as precursors to novel 4-aminotetrahydropyrazolo[3,4-b]quinolin-5-ones and N-(4-cyanopyrazol-5-yl)pyridine-3-carbonitrile

Abstract

We report an efficient synthesis of 4-aminotetrahydropyrazolo[3,4-b]quinolin-5-one derivatives via Friedländer-type reaction of dimedone with 5-aminopyrazole-4-carbonitriles in the presence of an acidic catalyst. We also report the synthesis of N-(1H-pyrazol-5-yl)- pyridine-3-carbonitrile via the reaction of pyrazol-5-ylcyanoacetamide with acetylacetone in the presence of basic catalyst.

Graphical Abstract

Keywords:

• 5-Amino-1-phenylpyrazole-4-carbonitrile
• 4-Aminopyrazolo[3,4-b]quinolin-5-ones
• dimedone
• N-(1H-pyrazol-5-yl)- pyridine-3-carbonitrile
• pyrazol-5-ylcyanoacetamide