Structure of the Salts of Aromatic Nitriles

Upson, Fred W.; Maxwell, Robert T.; Parmelee, Howard M.

doi:10.1021/ja01368a031

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“…Although the intermediates were not separated and characterized, an attempt was made to establish the mechanism for the formation of (Z)-acrylonitrile derivatives 2a-i and 4a-c in conformity with the previously reported analogous results (Scheme 4). 58,59 In order to optimize the reaction conditions, a model reaction was conducted using p-nitrophenylacetonitrile and 2,3-dimethoxy benzaldehyde (1b) under various reaction conditions (including varying the catalyst loading and the effect of the solvent in terms of yields and time). In order to establish the best reaction conditions, we performed an optimization study using a model substrate in the presence of varying amounts of silica chloride.…”

Section: Chemistrymentioning

confidence: 99%

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Stereoselective synthesis of Z-acrylonitrile derivatives: catalytic and acetylcholinesterase inhibition studies

et al. 2014

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In the present study, a focused library of (Z)-acrylonitrile analogues (library A & B) were synthesized, which were typically accessed via a facile Knoevenagel condensation between p-nitrophenylacetonitrile and appropriately substituted aromatic aldehydes (1a–i) and 3-formyl chromones (3a–c). This new synthetic eco-friendly approach resulted in a remarkable improvement in the synthetic efficiency (83–92% yield), high purity, minimizing the production of chemical wastes without using highly toxic reagents for the synthesis and, more notably, it improved the selectivity for (Z)-acrylonitrile derivatives. By performing DFT calculations, it was found that the (Z)-isomer of compound 2b is stabilized by 2.61 kcal mol−1 more than the (E)-isomer. All of the compounds were tested for acetylcholinesterase (AChE) inhibition. Compounds 2a and 4c, displayed the strongest inhibition, with IC50 values of 0.20 μM and 0.22 μM respectively. The methoxy group at the para-position of phenyl ring A was found to be essential for AChE inhibition.

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Section: Chemistrymentioning

confidence: 99%

“…The Cl is displaced selectively by the carbonyl oxygen of the aldehyde by a nucleophilic substitution reaction, generating a cationic centre on the carbonyl carbon, which is believed to be easily attacked by the nucleophile, i.e. the imide form of p -nitrophenylacetonitrile, 58 to give the corresponding acrylonitrile derivatives.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective synthesis of Z-acrylonitrile derivatives: catalytic and acetylcholinesterase inhibition studies

et al. 2014

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“…Some workers have maintained that the sodium salt of phenylacetonitrile exists entirely in the nitride form, C6H5CH=C=NNa(10).…”

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POTENTIAL ANALGESICS AND ANTISPASMODICS. I. THE SYNTHESIS OF OPEN-CHAIN ANALOGS OF DEMEROL¹

Tutwiler¹,

Child²,

Wrenn³

1954

J. Org. Chem.

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TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

Bergmann¹,

Ginsburg

Pappo

2011

Organic Reactions

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The Michael condensation in its original scope is the addition of an addend or donor containing an alpha‐hydrogen atom in the system OCCH to a carbon‐carbon double bond that forms part of a conjugated system of the general formula CCCO in an acceptor. The condensation takes place under the influence of alkaline reagents, typically alkali metal alkoxides. The range of addends is very broad. Typical acceptors are alpha, beta‐unsaturated aldehydes, keotnes, and acid derivatives. As an extension of the original scope, the Michael condensation has come to be understood to include addends and acceptors activated by groups other than carbonyl and carboxalkoxy. The wider scope is encompassed in this survey.

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Structure of the Salts of Aromatic Nitriles

Cited by 3 publications

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Stereoselective synthesis of Z-acrylonitrile derivatives: catalytic and acetylcholinesterase inhibition studies

Stereoselective synthesis of Z-acrylonitrile derivatives: catalytic and acetylcholinesterase inhibition studies

POTENTIAL ANALGESICS AND ANTISPASMODICS. I. THE SYNTHESIS OF OPEN-CHAIN ANALOGS OF DEMEROL¹

TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

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Structure of the Salts of Aromatic Nitriles

Cited by 3 publications

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Stereoselective synthesis of Z-acrylonitrile derivatives: catalytic and acetylcholinesterase inhibition studies

Stereoselective synthesis of Z-acrylonitrile derivatives: catalytic and acetylcholinesterase inhibition studies

POTENTIAL ANALGESICS AND ANTISPASMODICS. I. THE SYNTHESIS OF OPEN-CHAIN ANALOGS OF DEMEROL1

TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

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POTENTIAL ANALGESICS AND ANTISPASMODICS. I. THE SYNTHESIS OF OPEN-CHAIN ANALOGS OF DEMEROL¹