‘On-solvent’ new domino reaction of salicylaldehyde, malononitrile and 4-hydroxy-6-methylpyridin-2(1 H )-one: fast and efficient approach to medicinally relevant 4-pyridinyl-2-amino-4 H -chromene scaffold

Elinson, Michaïl N.; Ryzhkov, Fedor V.; Vereshchagin, A. N.; Korshunov, Alexander D.; Новиков, Роман А.; Egorov, Mikhail P.

doi:10.1016/j.mencom.2017.11.006

Cited by 22 publications

(10 citation statements)

References 33 publications

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“…In recent years, we have accomplished multicomponent syntheses of new heterocyclic systems using different types of 'one-pot' transformations of carbonyl compounds and C-H acids. [24][25][26][27] Recently, we carried out multicomponent transformations of salicylaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile and 3phenylisoxazol-5(4H)-one, 28 3-methyl-2-pyrazolin-5-one 29 and 6-hydroxy-4-methylpyridin-2(1H)-ones. 30 Furthermore, we have implemented multicomponent reactions of salicylaldehydes, two equivalents of malononitrile and 1,3-cyclohexanediones.…”

Section: Figure 2 Bioactive Molecules With Pyridin-2(1h)-one Moietymentioning

confidence: 99%

Pseudo-four-component synthesis of 5-(4-hydroxy-2-oxo-1,2-dihydropyridin-3-yl)-substituted 5H-chromeno[2,3-b]pyridines and estimation of its affinity to sirtuin 2

Ryzhkova¹,

Ryzhkov²,

Elinson³

et al. 2020

Arkivoc

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Multicomponent reactions (MCRs) are masterpieces of synthetic efficiency and reaction design which allow the rapid generation of complex molecules with biologically relevant scaffold fragments. A new pseudo-fourcomponent, one-pot synthetic scheme yielding 5-(4-hydroxy-2-oxo-1,2-dihydropyridin-3-yl)-substituted 5Hchromeno[2,3-b]-pyridines in 40-97% yields is reported. This 'one-pot' process opens an efficient and convenient way to substituted 5H-chromeno[2,3-b]pyridines, which are promising compounds for biomedical applications. Molecular docking studies of the synthesized 5H-chromeno[2,3-b]pyridines were carried out to identify their relationship with the binding pockets of sirtuin 2 (SIRT2).

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Section: Figure 2 Bioactive Molecules With Pyridin-2(1h)-one Moietymentioning

confidence: 99%

Pseudo-four-component synthesis of 5-(4-hydroxy-2-oxo-1,2-dihydropyridin-3-yl)-substituted 5H-chromeno[2,3-b]pyridines and estimation of its affinity to sirtuin 2

Ryzhkova¹,

Ryzhkov²,

Elinson³

et al. 2020

Arkivoc

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“…In continuation of our research on the multicomponent synthesis of alicyclic [38][39][40][41] and heterocyclic [42][43][44][45][46][47][48] derivatives from carbonyl compounds and C-H acids, we report the results of a novel one-pot five-component reaction between aromatic aldehydes, esters of 3-oxocarboxylic acid, nitriles and ammonium acetate for the direct highly stereoselective substituted 1,4,5,6-tetrahydropyridines formation.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective one-pot five-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines with two and three stereocenters

Vereshchagin¹,

Iliyasov²,

Karpenko³

et al. 2022

Arkivoc

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A novel five-component stereoselective synthesis of polysubstituted tetrahydropyridines is reported. The Knoevenagel condensation -Michael addition -Mannich reaction -cyclization -dehydration cascade of aldehydes, esters of 3-oxocarboxylic acids C-H acids and ammonium acetate provides convenient access to 2substituted alkyl (4SR,6RS)-4,6-diaryl-5,5-dicyano-1,4,5,6-tetrahydropyridi-ne-3-carboxylates with two stereocenters and 3,5-dialkyl (4RS, 5SR,6RS)-5-cyano-2,4,6-triaryl-1,4,5,6-tetrahydropyri-dine-5,3-carboxylates with three stereocenters in 57-84% yields. It was established that formation of products proceeds via substituted 2-hydroxypiperidines with four stereocenters. Ammonium acetate plays a dual role, acting as a base and as a nitrogen source. Five bonds are formed as a result of multicomponent process. Structures of new compounds were confirmed by 1 H, 13 C NMR, IR, and mass spectral studies. The formation of single diastereomers was confirmed by singe crystal X-ray diffraction studies and 2D-NMR spectroscopy.

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“…Subsequently, we studied the multicomponent synthesis of cyclic [ 49 , 50 , 51 ] and heterocyclic [ 52 , 53 , 54 , 55 , 56 ] compounds from carbonyls and C-H acids. The current research is dedicated to the pseudo-five-component synthesis of 1,4,5,6-tetrahydropyridines 4 , 5 directly from aromatic aldehydes 1 (both with electron-withdrawing and electron-donating substituents), cyano C-H acids 2 (malononitrile or ethyl cyanoacetate), esters of 3-oxocarboxylic acids 3 and ammonium acetate ( Scheme 2 , Table 1 ).…”

Section: Introductionmentioning

confidence: 99%

Tetrahydropyridines’ Stereoselective Formation, How Lockdown Assisted in the Identification of the Features of Its Mechanism

Vereshchagin¹,

Iliyasov²,

Karpenko³

et al. 2022

Molecules

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The multicomponent reaction of aldehydes, cyano-containing C-H acids, esters of 3-oxocarboxylic acid and ammonium acetate led to unexpected results. The boiling of starting materials in methanol for one to two hours resulted in the formation of polysubstituted 1,4,5,6-tetrahydropyridines with two or three stereogenic centers. During the 2020 lockdown, we obtained key intermediates of this six-step domino reaction. A number of fast and slow reactions occurred during the prolonged stirring of the reaction mass at rt. Sequence: 1. Knoevenagel condensation; 2. Michael addition; 3. Mannich reaction; 4. cyclization—fast reactions and cyclization of the product polysubstituted 2-hydroxypiperidine—was isolated after 40 min stirring at rt. Further monitoring proved the slow dehydration of 2-hydroxypiperidine to obtain 3,4,5,6-tetrahydropyridine after 7 days. Then, four-month isomerization occurred with 1,4,5,6-tetrahydropyridine formation. All reactions were stereoselective. Key intermediates and products structures were verified by X-ray diffraction analysis. Additionally, we specified conditions for the selective intermediates’ preparation.

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‘On-solvent’ new domino reaction of salicylaldehyde, malononitrile and 4-hydroxy-6-methylpyridin-2(1 H )-one: fast and efficient approach to medicinally relevant 4-pyridinyl-2-amino-4 H -chromene scaffold

Cited by 22 publications

References 33 publications

Pseudo-four-component synthesis of 5-(4-hydroxy-2-oxo-1,2-dihydropyridin-3-yl)-substituted 5H-chromeno[2,3-b]pyridines and estimation of its affinity to sirtuin 2

Pseudo-four-component synthesis of 5-(4-hydroxy-2-oxo-1,2-dihydropyridin-3-yl)-substituted 5H-chromeno[2,3-b]pyridines and estimation of its affinity to sirtuin 2

Stereoselective one-pot five-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines with two and three stereocenters

Tetrahydropyridines’ Stereoselective Formation, How Lockdown Assisted in the Identification of the Features of Its Mechanism

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