ChemInform Abstract: Synthesis of Decahydro‐1,7‐phenanthridinedione (III), (IV), (VII), and Hexahydro‐8‐isoquinolone Derivatives (IX), from 2‐Acetyl‐2‐cyclohexene‐1‐ones (I), (V) with Enamino Carbonyl Compounds (II), (VI), (VIII).

Ozols, Ya. Ya.; Пырко, А. Н.; Lakhvich, F. A.; Vı̄gante, Brigita; Dubure, R. R.; Dubur, G. Ya.; Akhrem, A. A.

doi:10.1002/chin.199035177

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“…It should be noted that the α, β-unsaturated carbonyl compound 3 is a latent form of the crossconjugated endion system of the easily react with enolic dienophiles via heterocyclization of Diels-Alder. At the same time, a pyran cycle is formed [20][21][22].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 4-(2-Hydroxyphenyl)-5,6,7,8-Tetrahydroisoxazolo [5,4-B]chromene-5(4h)-Ones

Pyrko¹

2018

IVUZKKT

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The aim of this work is the synthesis of new tetraheterocyclic compounds of interest as potential biologically active substances that include the isoxazole and chromone moieties in their structure. The synthesis of such compounds was carried out with two stages. By Knoevenagel condensation of 3-methyl-1,2-isoxazol-5(2H)-on with salicylic aldehyde (4Z)-4-(2-hydro-xybenzyliden)-3-methyl-1,2-oxazol-5(4H)-on was obtained. In this reaction an excess of half of the aldehyde equivalent was used to increase the yield of the product. Pyperidine was used as a catalyst. The reaction was carried out by boiling the components in ethyl acetate. The reaction of the resulting benzylidenisoxazole derivative with cyclohexane-1,3-dione or dimedone was performed by boiling the components in ethanol without the use of a catalyst. The interaction mechanism includes heterodiene Dielsa-Aldera condensation followed by dehydration of one water molecule. As a result, 3-methyl-4-(2-hydroxyphenyl-5,6,7,8-tetrahydroisoxazolo[5,4-b]chromene-5(4H)-one and 3,7,7-trimethyl-4-(2-hydroxyphenyl)-5,6,7,8,9-tetrahydroisoxazolo[5,4-b]chromen-5(4H)–one were obtained. Purification of the synthesized compounds was carried out by crystallization from ethanol. All the obtained compounds were characterised by IR 1H NMR and UV spectroscopies. In 1H NMR spectra there are signals of the methyl groups of the isoxazole ring of compounds at 2.26, 2.29, 2.34 ppm respectively. In the UV spectrum of a plane molecule of (4Z)-4-(2-hydroxybenzyliden)-3-methyl-1,2-oxazol-5(4H)-on there is a long-wave absorption maximum (400.9 nm) corresponding to the joint system of conjugated bonds of the isoxazole and aromatic rings. The structures of the obtained compounds were confirmed by high resolution mass-spectrometry analysis. In the spectra of 3-methyl-4-(2-hydroxyphenyl-5,6,7,8-tetrahydroisoxazolo[5,4-b]chromene-5(4H)-one and 3,7,7-trimethyl-4-(2-hydroxyphenyl)-5,6,7,8,9-tetrahydroisoxazolo[5,4-b]chromen-5(4H)–one the[M + Na]+ ion peaks were observed. The presence of fragment peaks [M + Na – CO]+ and [M + Na – CO – H2O]+ confirms the presence of hydroxy and carbonyl groups in the molecules.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 4-(2-Hydroxyphenyl)-5,6,7,8-Tetrahydroisoxazolo [5,4-B]chromene-5(4h)-Ones

Pyrko¹

2018

IVUZKKT

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show abstract

ChemInform Abstract: Synthesis of Decahydro‐1,7‐phenanthridinedione (III), (IV), (VII), and Hexahydro‐8‐isoquinolone Derivatives (IX), from 2‐Acetyl‐2‐cyclohexene‐1‐ones (I), (V) with Enamino Carbonyl Compounds (II), (VI), (VIII).

Cited by 1 publication

References 0 publications

Synthesis of 4-(2-Hydroxyphenyl)-5,6,7,8-Tetrahydroisoxazolo [5,4-B]chromene-5(4h)-Ones

Synthesis of 4-(2-Hydroxyphenyl)-5,6,7,8-Tetrahydroisoxazolo [5,4-B]chromene-5(4h)-Ones

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