Synthese von 6-Formyl-2-pyridincarbonitril

Eichinger, K.; Berbalk, H.; Kronberger, Hermann

doi:10.1055/s-1982-30085

Cited by 7 publications

(7 citation statements)

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“…We note that mono-oxidation of bis-methanol-pyridines to carboxaldehyde can also be achieved with MnO 2 as oxidant [34]. The known 2,6-disubsituted pyridines P3 [35][36][37] and P4 [36][37][38], which we planned to use in the synthesis of tetrazoles, were prepared from P1 (we described its multi-gram synthesis before [12]) by conversion of the carboxaldehyde into the carbonitrile P3 with NH 2 OHÁHCl in DMSO [39], and by oxidation of the pyridine-2-methanol to the carboxaldehyde P4 with SeO 2 (Scheme 3).…”

Section: Resultsmentioning

confidence: 90%

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Synthesis and spectroscopy of anionic tridentate benzimidazole-pyridine carboxylate and tetrazolate chromophore ligands

Shavaleev

Eliseeva

2015

Inorganica Chimica Acta

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Section: Resultsmentioning

confidence: 90%

“…Pale yellow solid: 446 mg (3.32 mmol; 61%; C 7 H 6 N 2 O; MW 134.14). It can be checked for the presence of DMSO by recording 1 P4: For alternative syntheses, see [36][37][38]. The reaction was performed under nitrogen.…”

Section: Synthesis Of Pyridinesmentioning

confidence: 99%

Synthesis and spectroscopy of anionic tridentate benzimidazole-pyridine carboxylate and tetrazolate chromophore ligands

Shavaleev

Eliseeva

2015

Inorganica Chimica Acta

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“…The starting material for the title compound was the commercially-available 6-cyano-2-methylpyridine. One portion of this was brominated using N-bromosuccinimide in the presence of UV-light to give the corresponding crystalline 6-cyano-2-dibromethylpyridine O) which was hydrolyzed with aqueous silver nitrate to form 6-cyano-2formylpyridine (2), as reported by Eichinger and co-workers in 1982 (15). This was methylated with sodium cyanoborohydride in the same manner as described above (14) to give the free base 3 as an oil.…”

Section: Synthesis Results and Discussionmentioning

confidence: 98%

“…The side chain reagent was prepared as described earlier(13). The intermediate starting 5,6-dimethoxy-4-methyl-8-nitroquinoline, available from earlier work, was prepared by well developed procedures(15). This was hydrogenated with Raney nickel catalyst to give the requisite 8-aminoquinoline 2 {87%).…”

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confidence: 99%

Synthesis of Improved Antileishmanial and Antitrypanosomal Drugs, Treatment and Prophylaxis

Markovac¹,

Dagli²,

Ash³

et al. 1989

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S. MONITORING ORGANIZATION REPORT NUMBER(S) 6a. NAME OF PERFORMING ORGANIZATION Ash Stevens Inc. 6b. OFFICE SYMBOL (If »pplicable) 7a. NAME OF MONITORING ORGANIZATION 6c ADDRESS (Oty, State, tod ilPCodt) 5861 John C. Lodge Freeway Detroit, Michigan 48202 7b. ADDRESS (C/ty. Star«, »no up Cod*) 8a. NAME OF FUNDING/SPONSORING ORGANIZATION U.S. Army Medical Research & Development Command 8b. OFFICE SYMBOL (If ipplicable) 9. PROCUREMENT INSTRUMENT IDENTIFICATION NUMBER DAMD17-8A-C-A210 8c ADDRESS (Oty, State, and ZIP Code

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“…The 6-(1,3-dioxolan-2-yl)-2-pyridinecarbonitrile ( 7f) (Scheme 5), derived from the known 6-cyano-2-pyridinecarboxaldehyde, was the common starting material in the synthesis of aldehydes 8h , k , l . At first, the nitrile function of 7f was activated as an imidoyl ether (not shown in Scheme 5) which, by reaction with ethylenediamine or cysteamine, afforded the imidazoline 7i and thiazoline 7j , respectively.…”

Section: Chemistrymentioning

confidence: 99%

Design and Synthesis of a Series of 6-Substituted-2-pyridinylmethylamine Derivatives as Novel, High-Affinity, Selective Agonists at 5-HT_1AReceptors

et al. 1998

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A search for novel, selective agonists with high intrinsic activity at the 5-HT1A subtype of serotonin (5-HT) receptors was undertaken. Mechanistic and thermodynamic considerations led to the design of 6-substituted-2-pyridinylmethylamine as a potential 5-HT1A pharmacophore. Various adducts derived from the 6-substituted-2-pyridinylmethylamine moiety were tested for their affinity at 5-HT1A, alpha1-adrenergic, and D2-dopaminergic receptors. Compounds with high affinity for 5-HT1A receptors (pKi >/= 8) were examined for agonist properties by measuring their ability to inhibit forskolin-stimulated cAMP production in HA7 cells (i.e., HeLa cells permanently transfected with the h5-HT1A receptor gene and expressing the h5-HT1A receptor protein). Several compounds of the type aryl¿4-[(6-substituted-pyridin-2-ylmethylamino)methyl]piperidin -1-yl¿ methanone had nanomolar affinity for 5-HT1A binding sites and were more than 500-fold selective with respect to alpha1 and D2 sites. Importantly, their 5-HT1A agonist properties were demonstrated in HA7 cells where they behaved as potent inhibitors of cAMP accumulation. In particular, (3, 4-dichlorophenyl)¿4-[(6-oxazol-5-ylpyridin-2-ylmethylamin o)methyl]pip eridin-1-yl¿methanone (70) and (3, 4-dichlorophenyl)¿4-[(6-azetidinopyridin-2-ylmethylamino)met hyl]piper idin-1-yl¿methanone (36) appeared to be more potent than, and at least as efficacious as, the prototypical 5-HT1A agonist (+/-)-8-OH-DPAT. SAR studies revealed that the pyridine nitrogen atom and the nature and the position of the substituents on the pyridine ring were critically involved in the ability of the compounds to recognize and activate 5-HT1A receptors. Structural modifications of the nonpharmacophoric part of the molecule showed, however, that the entire structure was required for affinity at 5-HT1A binding sites.

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Synthese von 6-Formyl-2-pyridincarbonitril

Cited by 7 publications

References 0 publications

Synthesis and spectroscopy of anionic tridentate benzimidazole-pyridine carboxylate and tetrazolate chromophore ligands

Synthesis and spectroscopy of anionic tridentate benzimidazole-pyridine carboxylate and tetrazolate chromophore ligands

Synthesis of Improved Antileishmanial and Antitrypanosomal Drugs, Treatment and Prophylaxis

Design and Synthesis of a Series of 6-Substituted-2-pyridinylmethylamine Derivatives as Novel, High-Affinity, Selective Agonists at 5-HT_1AReceptors

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Synthese von 6-Formyl-2-pyridincarbonitril

Cited by 7 publications

References 0 publications

Synthesis and spectroscopy of anionic tridentate benzimidazole-pyridine carboxylate and tetrazolate chromophore ligands

Synthesis and spectroscopy of anionic tridentate benzimidazole-pyridine carboxylate and tetrazolate chromophore ligands

Synthesis of Improved Antileishmanial and Antitrypanosomal Drugs, Treatment and Prophylaxis

Design and Synthesis of a Series of 6-Substituted-2-pyridinylmethylamine Derivatives as Novel, High-Affinity, Selective Agonists at 5-HT1AReceptors

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Design and Synthesis of a Series of 6-Substituted-2-pyridinylmethylamine Derivatives as Novel, High-Affinity, Selective Agonists at 5-HT_1AReceptors