The Chemistry of Derivatives of 2-Benzaltetralone. IV.¹ The Synthesis, Spectra and Ring Cleavage Reactions of Some Spiroepoxyketones

Five-Membered Heterocyclic Ring Via Dichalcones

“…spectra give a band of absorption at (992-1033 cm -1 ) due to the stretching of (C -O-C) in the peroxide ring and an absorption at (1669-1675 cm -1 ) of the stretching of the carbonyl group in addition to the band at (1621-1628 cm -1 ) due to the (C=C). We notice in this spectra that there is an increase shift in the magnitude of absorption of the carbonyl group in comparison with that of the prepared double chalcones (4)(5)(6)(7)(8)(9)(10)(11)(12) and this indicate the disappear of the conjugation in one of the two ends between the carbonyl group and one double bond. Pyrazoline compounds and their substitutes have grate importance not less than oxiranes , so these compounds were prepared by the reaction between chalcones (4-12) and hydrazine hydrate at room temperature.…”

“…Filter the precipitate ,wash with cold water until neutralization, collect the product, dry after recrystallization from ethanol. preparation of Epoxy chalcones (oxiranes)(13-21) [11][12][13] In around bottom flask , a mixture of (1 ml) of (10 %) sodium hydroxide and (0.1 mole) of (30 % ) hydrogen peroxide were added with continuous stirring using magnetic stirrer, a hot solution of (0.1mole) of the dichalcone (4-12) dissolved in (10 ml) ethanol. After complete addition, the mixture stirred for (3 hrs) at room temperature, then after (24 hrs) the precipitate was filtered ,washed with water until the neutralization and recrystallized from ethanol.…”

“…After complete addition, the mixture stirred for (3 hrs) at room temperature, then after (24 hrs) the precipitate was filtered ,washed with water until the neutralization and recrystallized from ethanol. preparation of (3-alkyl-5-aryl-2-pyrazoline)(22-30) [14][15] In a round bottom flask fitted with magnetic stirrer dissolve (0.005 mol) of any double chalcone (4)(5)(6)(7)(8)(9)(10)(11)(12) , and add (0.05 mol ,0.05 g) of hydrazine hydrate with stirring for (6 hrs) at room temperature. Filter the produced precipitate and wash with water then recrystallize from ethanol.…”

“…In this study some of dichalcone compounds (4)(5)(6)(7)(8)(9)(10)(11)(12) were prepared by the reaction of benzalacetone and its derivatives with a number of different ketones (acetophenone, acetanilide, 2butanone). Also a number of heterocyclic compounds were prepared as a derivatives of that dichalcones, these derivatives were prepared by the reaction of dichalcone with hydrogen peroxide, hydrazine hydrate and urea to produce oxirane compounds (13)(14)(15)(16)(17)(18)(19)(20)(21), pyrazolines (22)(23)(24)(25)(26)(27)(28)(29)(30) and pyrimidinones (31-40) respectively.…”

Synthesis of heterocyclic compounds by the reactions of exocyclic α,β‐unsaturated ketones

“…First examples for the epoxidation of unsubstituted 2-benzylidene-1-indanone (1) [17] and variously substituted 2-benzylidene-1-tetralones (2) [17,65,66] were published by Cromwell et al several decades ago. These α,β-enones were oxidized with alkaline hydrogen peroxide to afford the appropriate spiroepoxides.…”