Condensation of Hydroxynitroacetophenones with Aromatic Aldehydes in the Presence of Hydrogen Chloride

Széll, T.; Unyi, Rauscher É. M.

doi:10.1021/jo01039a515

Cited by 11 publications

(4 citation statements)

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“…Earlier work (8,9) had shown the 4-hydroxy derivative to be more reactive than 4-nitro-benzaldehyde and had also shown 'Part V I . T .…”

Section: Resultsmentioning

confidence: 97%

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New Nitrochalcones. Vii

Széll¹,

Eastham²,

Sipos³

1964

Can. J. Chem.

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SUMMARYA number of new nitrohydroxychalcones have been synthesized using sodium hydroxide and hydrogen chloride as catalysts. I t has been found that with substituents which increase the acidity of acetophenones or the electrophilic character of benzaldehydes (e.g. NOn, halogen, CN), sodium hydroxide is the better condensing agent, while with those substituents which increase the basic strength of the carbonyl, hydrogen chloride is satisfactory.

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“…Earlier work (8,9) had shown the 4-hydroxy derivative to be more reactive than 4-nitro-benzaldehyde and had also shown 'Part V I . T .…”

Section: Resultsmentioning

confidence: 97%

“…High concentrations of alkali should be avoided because of the possibility of Cannizzaro or other side reactions, especially with 2-or 4-nitro compounds (5,7,15,16). Side reactions seem less important in acid solution but can occur (8,16,19).…”

Section: Resultsmentioning

confidence: 99%

New Nitrochalcones. Vii

Széll¹,

Eastham²,

Sipos³

1964

Can. J. Chem.

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“…Prior to our own study, 197 time, E-3-Arylideneflavanones (E-34) were synthesized solely by the acid-catalyzed condensation of flavanones (33) and aromatic aldehydes (Scheme 17). [198][199][200][201][202][203][204][205] The reaction usually has been performed in alcoholic solution saturated with anhydrous hydrochloric acid at various temperatures and for different reaction times. For this condensation, use of glycine as catalyst was also described in one case.…”

Section: Scheme 15mentioning

confidence: 99%

Synthesis of exocyclic α,β-unsaturated ketones

Lévai

2003

Arkivoc

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This review describes synthetic procedures for the preparation of selected groups of the most important exocyclic α,β-unsaturated ketones. Some of these α,β-enones, víz. aurones and 3-benzylidene-4-chromanones belong to the natural products. The others are synthetic substances which are convenient and especially important intermediates for the stereoselective synthesis of polycyclic ring systems. To illustrate the utility of any special procedures, relevant examples have been included. However, it is not the aim of the present review article to list and evaluate all the papers published in this field. Owing to the huge number of papers, such a goal would be an almost unrealizable task.

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“…Recent interest in the 6-nitro-3-benzylideneflavanones as bacteriostatic materials has led us to reinvestigate the methods for their preparation (1)(2)(3)(4)(5)(6)(7). Reaction of the flavanone with the appropriate benzaldehyde in ethanol-hydrogen chloride according to von Kostanecki's method (1) was found to give best results.…”

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confidence: 99%