CCXLVII.—Substituted aromatic aldehydes in Hantzsch's pyridine condensation. Part II. Methyl- and nitro-benzaldehydes

Hinkel, Leonard Eric; Ayling, Ernest Edward; Morgan, William Henry

doi:10.1039/jr9310001835

Cited by 31 publications

(9 citation statements)

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“…The proposed structures of all products were confirmed by analytical and spectral data and by the spectralmelting points data spectra reported in previous works [7,8]. The analytical and spectral data of 6 were also consistent with the 1,2-dihydro isomeric system in which was evident from the resonance of the hydrogen joined attached to esters groups which they havecauses produces different shifts in the 1 H-nmr spectrum.…”

Section: Results Aand Discussionsupporting

confidence: 84%

“…The combination of 2-nitrobenzaldehyde 5 with ethyl acetoacetate however yielded interesting results. By sSeparation of the products with using column chromatography we obtainyielded as products the normal isomeric dihydropyridines 2 [8] and 7 , as crystalline solids in 35% and 20 % yields, and the compounds 8 and 9 in yields of 15% and 20%, respectively (Scheme 2). …”

Section: Results Aand Discussionmentioning

confidence: 99%

“…Recently we reported the preparation of 4-substituted-2-cyclo-hexenones by reductive cyclization of Hantszch esters using sodium and withand ethanol as the solvent [5]. As a part of our drug design program on drug design [6], we were interested to in the preparation ofprepare and evaluated the 1,4-dihydropyridines 1 and 2 [8] and evaluatethe evaluation of as their antihypertensive compounds properties, because since they are structurally similar to Nifedipine ( 3 ). In this paper we describe the results obtained when we tried attempted to get synthesisesynthesis of ze 1 and 2 from using the Hantzsch reaction of 5-hydroxy-2-nitrobenzaldehyde ( 4 ) and 2-nitrobenzaldehyde ( 5 ), respectively.…”

Section: Introductionmentioning

confidence: 99%

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Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

et al. 2001

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The reaction of 5-hydroxy-2-nitrobenzaldehyde with ethyl acetoacetate in ammonia gave the two expected isomeric 1,4- and 1,2-dihydropyridines resulting from the normal Hantzsch reaction. However, the combination of 2-nitrobenzaldehyde with ethyl acetoacetate under the same conditions yielded four products: the two normal isomeric dihydropyridines and two tricyclic compounds. When we attempted to independently synthesize the two tricyclic compounds by reductive cyclization of 4-(2-nitrophenyl)-2,6-dimethyl-3,5-dicarbetoxy-1,4-dihydropyridine and 2-(2-nitrophenyl)-4,6-dimethyl-3,5-dicarbetoxy-1,2-dihydropyridine with tin (II) chloride in hydrochloric acid media, we obtained instead an indole and a quinoline derivative, respectively.

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Section: Results Aand Discussionsupporting

confidence: 84%

Section: Results Aand Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

et al. 2001

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“…Generally 'claycop' gives higher yield than 'clayfen', but it requires a little longer reaction period. 101-102 [20] 75 [21] 63 [23] 115 [23] 86-87 1241 …”

Section: Aromatization Of 1cdihydropyridines By Clay-supported Metalmentioning

confidence: 99%

Aromatization of 1,4‐Dihydropyridines by Clay‐Supported Metal Nitrates

Balogh¹,

Hermecz²,

Ménszáros³

et al. 1984

Helvetica Chimica Acta

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“…Hinkel et al first observed that dihydropyridine derivatives are sensitive to UV light [3]. Berson and Brown reported that the photochemical conversion of 4-(o-nitrophenyl)-1,4-dihydropyridines produces the corresponding 4-(o-nitrosophenyl)pyridines [4].…”

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confidence: 99%