Reformatsky Reaction of 1-Aryl-3-(2-hydroxyphenyl)prop-2-en-1-ones with Methyl 1-Bromocyclohexanecarboxylate

1-Aryl-3-(2-hydroxy-5-R-phenyl)prop-2-en-1-ones reacted with the Reformatsky reagent derived from methyl 1-bromocyclohexanecarboxylate to give 4-(2-aryl-2-oxoethyl)-6-R-2 H ,4 H -spiro[[1]benzopyran-3,1′-cyclohexan]-2-ones. The products are formed as a result of intramolecular cyclization of the add...

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Published inRussian journal of organic chemistry Vol. 56; no. 12; pp. 2074 - 2078
Main Authors Nikiforova, E. A., Baibarodskikh, D. V., Kirillov, N. F., Dmitriev, M. V., Zverev, D. P.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.12.2020
Springer Nature
Springer Nature B.V
Subjects
Aromatic compounds
Carbon
Carbonyls
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Organic Chemistry
Physical Sciences
Reagents
Science & Technology
Reformatsky reaction
spiro heterocycles
spiro chromanones
hydroxy chalcones
1-bromocyclohexanecarboxylate
1-bromocycloalkanecarboxylates
chroman-2-ones
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Summary:1-Aryl-3-(2-hydroxy-5-R-phenyl)prop-2-en-1-ones reacted with the Reformatsky reagent derived from methyl 1-bromocyclohexanecarboxylate to give 4-(2-aryl-2-oxoethyl)-6-R-2 H ,4 H -spiro[[1]benzopyran-3,1′-cyclohexan]-2-ones. The products are formed as a result of intramolecular cyclization of the adduct of the organozinc reagent and substituted chalcone via nucleophilic attack of the phenoxide oxygen atom on the ester carbonyl carbon atom. No cyclization products resulting from attack of the enolate oxygen atom on the ester carbonyl carbon atom were detected.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428020120040