A High‐Yielding Preparation of β‐Ketonitriles.

Ji, Yaohui; Trenkle, William C.; Vowles, James V.

doi:10.1002/chin.200629045

Cited by 2 publications

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“…The starting materials, 3-(substituted)-5-aminopyrazoles, required for the synthesis of the title compounds were synthesized by the condensation of appropriate β-ketonitriles with hydrazine monohydrate according to the literature procedure . The aminopyrazoles ( 6a – o ) were reacted smoothly with diethyl ethoxymethylenemalonate (DEEM) in glacial acetic acid to give the cyclized ethyl 2-substituted-4,7-dihydro-7-oxopyrazolo[1,5- a ]pyrimidine-6-carboxylates ( 7a – o ) in good yields.…”

Section: Chemistrymentioning

confidence: 99%

Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists

et al. 2013

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We recently described the medicinal chemistry of a new series of heteroaryl-4-oxopyridine/7-oxopyrimidines as CB2 receptor partial agonists, showing that the functionality of these ligands is controlled by the nature of the heteroaryl function condensed with the pyridine ring. We describe herein the design and synthesis of the 7-oxopyrazolo[1,5-a]pyrimidine-6-carboxamides, structural isomers of our previously reported pyrazolo[3,4-b]pyridines. All of the new compounds showed high affinity and selectivity for the CB2 receptor in the nanomolar range. In 3,5-cyclic adenosine monophosphate (cAMP) assays, the novel series shows stimulatory effects on forskolin-induced cAMP production acting as inverse agonists.

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Section: Chemistrymentioning

confidence: 99%

Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists

et al. 2013

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“…Very recently, the reaction of sterically hindered nitriles with enolizable and nonenolizable esters was successfully achieved using 3 equiv. of potassium tert-amoxide (KO t Amyl) giving the corresponding *Corresponding authors (email: xufan@suda.edu.cn; qshen@suda.edu.cn) β-ketonitriles in high yields [12].…”

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confidence: 99%

Acylation of nitriles to β-ketonitriles catalyzed by a heterometallic alkoxide cluster of neodymium and sodium: NdNa8(O t Bu)10(OH)

Liu

Sheng

et al. 2011

Chin. Sci. Bull.

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Catalytic acylation of nitriles with esters in the presence of 10 mol% NdNa 8 (O t Bu) 10 (OH) is developed. The procedure is suitable for both enolizable and nonenolizable esters and affords β-ketonitriles in moderate to high yields. The heterometallic alkoxide cluster NdNa 8 (O t Bu) 10 (OH) is structurally characterized by X-ray diffraction, and a mechanism for the production of β-ketonitriles using the cluster is proposed and verified. Recently we found that the clusters [Ln 2 Na 8 (OCH 2 CH 2 -NMe 2 ) 12 (OH) 2 ](Ln=Nd, Pr, Sm, Y, Ho) are active singlecomponent catalysts for the polymerization of ε-caprolactone as well as trimethylene carbonate. The reactivity of these clusters is much higher than those of the related lanthanide alkoxide and sodium alkoxide compounds, indicating that a cooperative effect may exist between the two different metals in these ring-opening polymerization reactions [13]. These results encouraged us to study further the application of heterometallic alkoxide clusters containing lanthanide and sodium in organic synthesis. Here, we report the synthesis of heterometallic tert-butoxide clusters containing lanthanide and sodium LnNa 8 (O t Bu) 10 (OH) (Ln=Nd, Sm, Yb) and their catalytic activity for the acylation of nitriles with esters.

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A High‐Yielding Preparation of β‐Ketonitriles.

Abstract: Nitriles P 0350A High-Yielding Preparation of β-Ketonitriles. -The synthetically useful target compounds are prepared in excellent yields via the reaction of nitriles with esters. -(JI, Y.; TRENKLE*, W. C.; VOWLES,

Cited by 2 publications

References 1 publication

Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists

Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists

Acylation of nitriles to β-ketonitriles catalyzed by a heterometallic alkoxide cluster of neodymium and sodium: NdNa8(O t Bu)10(OH)

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A High‐Yielding Preparation of β‐Ketonitriles.

Abstract: Nitriles P 0350A High-Yielding Preparation of β-Ketonitriles. -The synthetically useful target compounds are prepared in excellent yields via the reaction of nitriles with esters. -(JI, Y.; TRENKLE*, W. C.; VOWLES,

Cited by 2 publications

References 1 publication

Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB2 Cannabinoid Receptor Inverse Agonists

Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB2 Cannabinoid Receptor Inverse Agonists

Acylation of nitriles to β-ketonitriles catalyzed by a heterometallic alkoxide cluster of neodymium and sodium: NdNa8(O t Bu)10(OH)

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Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists

Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists