405. The lability of the dimethylamino-group in some dimethylamino-ketones

Jacob, Anni; Madinaveitia, J.

doi:10.1039/jr9370001929

Cited by 8 publications

(4 citation statements)

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“…This reaction is of considerable preparative value, as numerous aromatic or heterocyclic amines can be used in the transamination stage. Compound 17c was identical (m. p., mixed m. p., and spectral data) with an authentic sample obtained by treating 14a with phenylhydrazine according to an earlier report .…”

Section: Resultssupporting

confidence: 57%

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Utility of Ketonic Mannich Bases in Synthesis of Some New Functionalized 2‐Pyrazolines

Afsah

Keshk

Abdel-Rahman

et al. 2017

Journal of Heterocyclic Chem

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The styryl ketonic Mannich base 2 has been used as a precursor in the synthesis of 2‐pyrazolines having a basic side chain at C‐3 and a phenolic Mannich base at C‐5. Treatment of the bis(styryl ketonic bases) 6a and 8a with phenylhydrazine affords the bis(3‐functionalized 2‐pyrazolines) 7 and 9. The transamination between the styryl keto base 10 and 4‐aminoantipyrine leads to 12, which reacts with piperazine to give 13. N‐Nitrosation of the sec‐Mannich bases 15a–d followed by reductive cyclization affords 2‐pyrazolines 17a–d. The keto base 14b has been used for the synthesis of 2‐pyrazolines having a phenolic Mannich base at C‐3 and its reaction with 3,5‐dimethyl‐1H‐pyrazole affords 23. The alkylation of 3‐methyl‐1‐phenyl‐2‐pyrazolin‐5‐one with the bis(Mannich base) 25 was investigated.

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Section: Resultssupporting

confidence: 57%

“…Compounds 8b , 12 , and 18a are of limited solubility in common 1 H NMR solvents. Compounds 3 , 15a – d , 17c , and 25 were prepared as previously described.…”

Section: Methodsmentioning

confidence: 99%

Utility of Ketonic Mannich Bases in Synthesis of Some New Functionalized 2‐Pyrazolines

Afsah

Keshk

Abdel-Rahman

et al. 2017

Journal of Heterocyclic Chem

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“…One of the three compounds with structures related to strychnine (Figure 1), 3[dimethyl-aminomethyl]indole (gramine) was obtained from Aldrich. The other two were synthesized as follows: 3-methylindole,2-butyrolactam, by acid catalysed rearrangement of the monophenylhydrazone of 2methyl,1,3-cylcohexanedione (Merling, 1894;Teuber et al, 1964) and 3-methyoxy-methyl-indole from gramine methiodide by methoxide substitution (Jacob & Madinaveitia, 1937;Schram, 1951).…”

Section: Synthesismentioning

confidence: 99%

An evaluation of the structure‐activity relationships of a series of analogues of mephenesin and strychnine on the response to pressure in mice

Bowser-Riley

Daniels²,

Hill³

et al. 1989

British J Pharmacology

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AB9 lAS 1 A range of compounds structurally related to the centrally acting muscle relaxant mephenesin and to the chemical convulsant strychnine were synthesized and tested for their ability to alter the threshold pressures for the onset of high pressure convulsions in mice. 2 The ability of both groups of compounds to alter the threshold pressures for convulsions was found to be dependent on the nature of a simple molecular skeleton. Thus, compounds that possessed a negatively polarized group located both in the same plane as and some 4.5 A from an aromatic nucleus increased the thresholds whereas compounds with a positively polarized group at the same location reduced the thresholds. 3 These findings support the suggestion that pressure elicits convulsions via a selective action on a receptor protein complex rather than via some general perturbation of the lipid regions of cellular membranes.

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“…prtpmitiori o f rY-uri.substituted compounds bt:c,ausc. thv wavtioiih with hydrazinv itself are more complex arid lid to poor rc:ac.tiori conditions and low yields (5). Certain substitutc~d pyrazolincs were also obtained from the r w ction o f kt:tazinc.s with maleic or oxalic acid (6).…”

mentioning

confidence: 99%