Title: Synthesis of novel spiro pyrazolo-1,4-dihydropiridine via one-pot four-component reaction

Biography:

Bahman Ebrahimi Saatloo was born in Urmia (Iran) in 1979. He received his B.Sc in Applied Chemistry (2007) from the Urmia University. He will receive his Ph.D. degree in Organic Chemistry from the Urmia University (Iran) in 2017 after completing his research in the Study of Synthesis of Polyazadodecahedrone and Synthesis of Spirooxindole Compounds of 1,2,3,4- Tetrahydroqunoline by Base, Acid and Nano Catalysts under the guidance of Professor Mohammad Mehdi baradarani. His current research interest focuses on the synthesis of Spirooxindole and supramolecular in heterocyclic for organic synthesis.

Abstract

Green synthesis of spiropyrazolo-1,4-dihydropyridine has been reported via one-pot four-component reaction in EtOH/H₂O (1:9) in the presence of p-TSA as a catalyst.

Spirooxindoles are classified as an important structural motif due to their distribution in diverse natural products, biologically and pharmaceutical activities such as the influenza virus [1], as inhibitors of the dengue virus and anti-cancer agents [2]. Therefore, we conducted a series of examination the chemistry of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolone-1,2-dione, in which the reactivity of  the ketone carbonyl group of the 2-keto-amide unit was utilized. Thus, we were able to construct various spiro [3,3’-oxindoles] via three and four component combination [3]. Amongst, Spiropyrazole-1,4-dihydropyridine moieties have shown important biological and medicinal activities.

As a part of our ongoing interest in this context, we reported a simple and facile synthesis of a new type of spiropyrazolo-1,4-dihydropyridines (5) in the presence of p-TSA as a catalyst (scheme 1) from starting materials phenyl hydrazine hydrochloride derivatives (3), 3-aminobut-2-enenitrile (2), 3-oxo-3-phenyl propanenitrile (4) and 5,6-dihydro-1H-pyrrolo[3,2,1-ij]quinolone 1,2(4H)-dione (1) in environmentally friendly solvent, EtOH/H₂O.