Regioselective reaction of ortho-piperidinobenzaldehydes with pyrazolone

Platonova, A. Yu.; Deeva, E. V.; Zimovets, O. A.; Shatunova, D. V.; Eltsov, Oleg S.; Слепухин, П. А.; Глухарева, Т. В.; Morzherin, Yu. Yu.

doi:10.1007/s11172-011-0151-6

Cited by 5 publications

(2 citation statements)

References 17 publications

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“…Examination of the cyclization under alternative literature procedures was made, but refluxing in either n -butanol at 117 °C or in EtOH/H 2 O, or adding pyrrolidine as a catalyst, resulted in either lower yield or no isolated product.…”

Section: Resultsmentioning

confidence: 99%

Spirocyclic Tetramates by Sequential Knoevenagel and [1,5]-Prototropic Shift

et al. 2019

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Spirocycles; Tetramates; Antibacterial Highly functionalised spirocyclic tetramates were prepared via a sequential Knoevenagel reaction and [1,5]-prototropic shift (Treaction) of bicyclic tetramates. While these compounds isomerise in solution, stable analogues can be prepared via appropriate choice of substituents. Further modification of these compounds allows for introduction of aromatic groups, making them suitable as skeletons suitable for application in medicinal chemistry.

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Section: Resultsmentioning

confidence: 99%

Spirocyclic Tetramates by Sequential Knoevenagel and [1,5]-Prototropic Shift

et al. 2019

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“…In 2011, the Morzherin group reported a tandem Knoevenagel condensation/ tert ‐amino effect cyclization between N ‐protected pyrazolone 8 a and ortho ‐piperidinobenzaldehydes 59 by using 1‐butanol as solvent and pyrrolidine (10 mol %) as catalyst with 6 hours reflux (Scheme ) . Different substituents at different positions of ortho ‐piperidinobenzaldehydes were effective in this reaction, yielding the seven corresponding spirocompounds 60 in accepted to outstanding yields (38–97 %).…”

Section: Organocatalytic Asymmetric Synthesis Of Spiropyrazolones Fusmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Spiropyrazolones and their Application in Medicinal Chemistry

Xie

Peng

et al. 2019

The Chemical Record

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Chiral spiropyrazolones are unique frameworks widely found in a large family of medicinally relevant compounds with various biological activities. Substantial research efforts have been invested toward stereoselectively by constructing spiro‐cyclic structures. Over the past years, remarkable progress has been made in the organo‐ and metal‐catalyzed asymmetric synthesis of spiropyrazolones through the utilization of accessible simple pyrazolone derivatives as raw materials. This review is organized according to the size of the spiro‐ring fused at the 4‐position of the pyrazolone framework. In the last part, the bio‐evaluations of chiral spiropyrazolones for drug discovery are summarized.

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