N-aryl-2-hydroxy-1,2,3,4-tetrahydropyridines and N-aryl-2-chloromethylene-1,2,3,4-tetrahydropyridines — successive intermediates in the Hantzsch synthesis of 1,4-dihydropyridines

Chekavichus, B. S.; Popelis, Yu. Yu.; Shebenina, E.; Sausin'sh, A.; Verkhe, R.; Дубурс, Г.

doi:10.1007/bf02253029

Cited by 4 publications

(2 citation statements)

References 6 publications

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“…Compound 1a, and the other N-phenyl-dihydropyridines (1b-1e), were synthesized from the appropriate enamines and enones, as described by Chekavichusie. 22 The 4-aryl-1,4-dihydropyridines 1g and 1h were prepared through the classic multicomponent Hantzsch synthesis, 23 and N-methyldihydropyridine 1f was obtained by a methylation reaction from 1g, according to Lusis et al 12a (for details, see Supplementary information). For our delight, BF 3 OEt 2 was capable of converting all dihydropyridines evaluated in their correspondent pyridinium salts or pyridines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of pyridinium salts from N-substituted dihydropyridines with BF3OEt2 in the absence of added oxidants

Guanaes

Ducatti

Duarte

et al. 2015

Tetrahedron Letters

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Section: Introductionmentioning

confidence: 99%

Synthesis of pyridinium salts from N-substituted dihydropyridines with BF3OEt2 in the absence of added oxidants

Guanaes

Ducatti

Duarte

et al. 2015

Tetrahedron Letters

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“…The formation of a similar exocyclic C=C bond was noted only on trying to alkylate N-substituted 1,4-dihydropyridines in the presence of a strong base (lithium diisopropylamide) [20] capable of deprotonating a methyl group. In some cases the presence of 2-methylene-1,2,3,4-tetrahydropyridines was also demonstrated as an intermediate products in the Hantzsch synthesis of N-substituted, as well as N-unsubstituted, dihydropyridines according to [21][22][23][24].…”

mentioning

confidence: 99%

Electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines

Turovska

Goba

Turovskis

et al. 2008

Chem Heterocycl Comp

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The electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines has been studied in an aprotic medium and in the presence of pyridine. In an aprotic medium the products of oxidation are both 4-alkyl-substituted and 4-unsubstituted pyridines or mixtures of them. On oxidation in acetonitrile of 4- 2,3, were obtained in addition to the oxidized forms. In the presence of base the products of preparative electrolysis of the studied compounds were 4-alkyl-substituted pyridines. The exception was the 4-i-Prsubstituted dihydropyridine which was dealkylated on oxidation even in the presence of base.Dihydropyridines are one of the most investigated classes of organic compounds. The synthesis and reactions of 1,4-dihydropyridines have been examined in detail in reviews [1][2][3][4]. Many compounds of this series possess pharmacological activity. A series of pharmaceuticals [5] has been developed based mainly on 4-arylsubstituted 1,4-dihydropyridines. Antioxidant properties have also been confirmed for the heterocycle itself in reactions with various radicals [6,7]. On the other hand study of the redox reaction of the dihydropyridine ring is also important for the reason that its oxidation is the main metabolism of dihydropyridines.The attention of electrochemists is mainly attracted [8][9][10][11][12][13] by the oxidation of 4-methyl-, 4-aryl-1,4-dihydropyridines or those unsubstituted in position 4. In all the mentioned cases proton is split off from the position 4 of the ring on oxidation. N Me H Me R H COOMe MeOOC 1-5 1 R = Me, 2 R = Et, 3 R = n-Pr, 4 R = i-Pr, 5 R = i-Bu

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ChemInform Abstract: N‐Aryl‐2‐hydroxy‐1,2,3,4‐tetrahydropyridines and N‐Aryl‐2‐chloromethylene‐1,2,3,4‐tetrahydropyridines — Consecutive Intermediates in the Hantzsch Synthesis of 1,4‐Dihydropyridines.

Chekavichus¹,

Popelis²,

Shebenina³

et al. 1998

ChemInform

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N-aryl-2-hydroxy-1,2,3,4-tetrahydropyridines and N-aryl-2-chloromethylene-1,2,3,4-tetrahydropyridines — successive intermediates in the Hantzsch synthesis of 1,4-dihydropyridines

Cited by 4 publications

References 6 publications

Synthesis of pyridinium salts from N-substituted dihydropyridines with BF3OEt2 in the absence of added oxidants

Synthesis of pyridinium salts from N-substituted dihydropyridines with BF3OEt2 in the absence of added oxidants

Electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines

ChemInform Abstract: N‐Aryl‐2‐hydroxy‐1,2,3,4‐tetrahydropyridines and N‐Aryl‐2‐chloromethylene‐1,2,3,4‐tetrahydropyridines — Consecutive Intermediates in the Hantzsch Synthesis of 1,4‐Dihydropyridines.

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