Synthesis and Hypotensive Activity of Some Heterocyclic Analogues of GYKI‐12 743

Mátyus, Péter; Kasztreiner, E.; Diesler, E.; Behr, Ágnes; Varga, Ildikó; Kosary, J.; Rablóczky, G.; Jaszlits, L.

doi:10.1002/ardp.19943270902

Cited by 5 publications

(5 citation statements)

References 5 publications

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“…Goel and col. have reported a one pot regioselective synthesis of 2-aminopyridines and 2-pyridones through nucleophile-induced ring transformation of 2-pyranones by urea in good yields [72]; to the best of their efforts, no selectivity is obtained and 1:1 mixtures are isolated following the reaction mechanism depicted in Scheme (9). The nitrile functionality present on the 2-pyranone is playing a role in the preparation of 2-amino pyridine.…”

Section: From Other Aromatic Heterocyclic Ringsmentioning

confidence: 99%

“…Over the last decade, natural compounds depicting this structure have emerged as potent pharmacological (see for example [2][3][4][5][6][7][8][9][10][11][12]) and agrochemical activities (see for example [13][14][15][16][17]). Over the last decade, natural compounds depicting this structure have emerged as potent pharmacological (see for example [2][3][4][5][6][7][8][9][10][11][12]) and agrochemical activities (see for example [13][14][15][16][17]).…”

Section: Introductionmentioning

confidence: 99%

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New Synthetic Methods to 2-Pyridone Rings

Torres¹,

Gil²,

Parra

2005

COC

202

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The synthesis of a substituted 2-pyridone ring is a topical area of continuing interest due to the number of biologically active molecules containing this moiety. Over the last decade, natural compounds with this structure have emerged as potent antitumor antiviral and attention, because those compounds may be studied as a simple model for investigating mechanisms of some enzymatic reactions or for discerning the behavior of nucleic acids bases in connection with mutation due to base mispairing or other mistaken helices. Recent studies have shown the usefulness of 2-pyridones as intermolecular connectors between building blocks in material science. Thus, despite the large number of methods known for their synthesis, new procedures are continuously being developed. Two main synthetic approaches can be found in the literature: from other heterocycles systems or condensation of acyclic systems. The latter can be further classified depending on the bond formed in the cyclization step: by C-C or C-N bond generation. The latter can be subclassified depending on the first condensation step. This is a review of new or improved methods for constructing 2-pyridone rings. This article will be restricted to ring formation, which can be included in the total synthesis of several compounds with specific biological or material properties.The pursuit of these properties requires efficient synthetic routes that allow rapid assembly and variation of multiple pendant substituents on the heteroaromatic case, which permits rapid analogsynthesis (RAS) [1].

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Section: From Other Aromatic Heterocyclic Ringsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Synthetic Methods to 2-Pyridone Rings

Torres¹,

Gil²,

Parra

2005

COC

202

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“…N -Substituted 2-pyridinones have been employed as active ingredients in drugs for the therapy of fibrotic disease and have been evaluated as inhibitors of human leukocyte elastase . Some synthetic 2-pyridinones have also demonstrated high hypotensive activity or cardiotropic activity . For these reasons, the synthesis of compounds containing a 2-pyridinone substructure has become increasingly important in a variety of medical applications.…”

Section: Introductionmentioning

confidence: 99%

Cyclobutenedione-Based Method for the Synthesis of Substituted 2-Pyridinones and Dihydro-2-pyridinones

Zhang

Liebeskind

1999

J. Org. Chem.

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Addition of N-Boc-protected R-amino carbanions to cyclobutenediones followed by methylation of the resulting alkoxides generated 4-(1-N-Boc-aminoalkyl)-4-methoxy-3-cyclobutenones. Removal of the Boc protecting group and thermal ring expansion gave dihydro-2-pyridinones in good yields. Treatment of the dihydro-2-pyridinones with NBS/pyridine led to the formation of the corresponding 2-pyridinones. This methodology proved general with regard to both the cyclobutenediones and R-amino carbanions.

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“…2 Molecules embedded with these scaffolds are known to exhibit diverse pharmacological activities as neuropeptide Y1 receptor antagonists, 3 muscle relaxants, 4 antitumor, 5 antifungal, 6 and antiviral 7 activities, free radical scavenging, 8 hypotensive, 9 and cardiotropic 10 activities, and inactivation of voltage-dependent K + channels. 11 From a chemical perspective, several dialkylaminopyridines such as DMAP, 4-pyrrolidinopyridine (PPY) and their analogues have been extensively used as catalysts in acylation and alkylation 12 reactions.…”

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confidence: 99%

Substituent-Dictated Concise Synthesis of 4,6-DisubstitutedN-Alkyl-2-pyridones and 2-Aminopyridines

Goel¹,

Singh²,

Verma³

2005

Synlett

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Functionalized N-alkyl-2-pyridones and 2-aminopyridines are useful precursors for the synthesis of various heterocyclic compounds of therapeutic importance. In this paper we have delineated and illustrated a direct methodology for the synthesis of 6-aryl-N-hydroxyethyl-4-methylsulfanyl-2-pyridones through the ring transformation of 6-aryl-3-cyano-4-methylsulfanyl-2H-pyran-2-ones by ethanolamine. Surprisingly, the analogous reaction with 6-aryl-3-cyano-4-piperidin-1-yl-2H-pyran-2-ones afforded 2-aminopyridines in high yield instead of the corresponding 2-pyridones.Substituted N-alkyl-2-pyridones and 2-aminopyridines in a flexible or rigid conformation are common structural features found in many biologically important synthetic and natural products. 2 Molecules embedded with these scaffolds are known to exhibit diverse pharmacological activities as neuropeptide Y1 receptor antagonists, 3 muscle relaxants, 4 antitumor, 5 antifungal, 6 and antiviral 7 activities, free radical scavenging, 8 hypotensive, 9 and cardiotropic 10 activities, and inactivation of voltage-dependent K + channels. 11 From a chemical perspective, several dialkylaminopyridines such as DMAP, 4-pyrrolidinopyridine (PPY) and their analogues have been extensively used as catalysts in acylation and alkylation 12 reactions. In addition, 2-aminopyridines and 2-pyridinones are key intermediates in the synthesis of a variety of heterocyclic compounds of therapeutic importance. 13In general, the alkylation of 2-pyridone leads to both Nand O-alkylated product and the regioselectivity depends on the nature of the base, the structure of the alkyl halide, substituents on the pyridone ring, and the solvent employed. 14 Selective N-alkylation of 2-pyridone predominates in the presence of sodium salts but an increase in the size of alkyl halide favors O-alkylation. Numerous synthetic methodologies are available for the synthesis of 2-pyridones 15-22 but the methods for direct access to Nalkyl-2-pyridones are rare. Similarly, various approaches are known in the literature for the synthesis of aminopyridines. [23][24][25] Recently, we reported a regioselective approach to access 2-pyridones and 2-aminopyridines through nucleophile-induced ring transformation of 2H-pyran-2-ones using urea as the nucleophilic source. 26Though palladium-catalyzed amination has been shown 27,28 to be of immense value as an alternative approach to preparing aminopyridines, the applicability of several of these methods suffers from a lack of generality, intolerance of many functional groups, or incompatibility with ring or N-alkyl chain substitution. Due to the difficulty in selective N-alkylation of 2-pyridone and the limitations of existing methodologies, we sought to develop a general synthetic route, which could directly provide Nalkylated pyridones and 2-aminopyridines. Herein, we report a one-pot synthesis of N-hydroxyethyl-2-pyridones and 2-aminopyridines through nucleophile-induced ring transformation of 2H-pyran-2-ones by ethanolamine.The 2H-pyran-2-ones 1a-e used as parent pre...

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Synthesis and Hypotensive Activity of Some Heterocyclic Analogues of GYKI‐12 743

Cited by 5 publications

References 5 publications

New Synthetic Methods to 2-Pyridone Rings

New Synthetic Methods to 2-Pyridone Rings

Cyclobutenedione-Based Method for the Synthesis of Substituted 2-Pyridinones and Dihydro-2-pyridinones

Substituent-Dictated Concise Synthesis of 4,6-DisubstitutedN-Alkyl-2-pyridones and 2-Aminopyridines

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Synthesis and Hypotensive Activity of Some Heterocyclic Analogues of GYKI‐12 743

Cited by 5 publications

References 5 publications

New Synthetic Methods to 2-Pyridone Rings

New Synthetic Methods to 2-Pyridone Rings

Cyclobutenedione-Based Method for the Synthesis of Substituted 2-Pyridinones and Dihydro-2-pyridinones

Substituent-Dictated Concise Synthesis of 4,6-DisubstitutedN-Alkyl-2-­pyridones and 2-Aminopyridines

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Substituent-Dictated Concise Synthesis of 4,6-DisubstitutedN-Alkyl-2-pyridones and 2-Aminopyridines