Reaction of 3-(3-arylacryloyl)-2H-chromen-2-ones with methyl 1-bromocyclopentanecarboxylate and zinc

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Abstract

The Reformatsky reagent, derived from the methyl 1-bromocyclopentanecarboxylate and zinc, selectively attaches to the double carbon-carbon bond of the heterocyclic fragment 3-(3-arylacryloyl)-2H-chromen-2-ones, resulting after hydrolysis of the reaction mixture the adducts that exist in enolic form. The structure of the adducts was confirmed by X-ray diffraction analysis. The addition to the carbon-carbon bond of the acryloyl fragment or the intramolecular cyclization of the adducts was not detected, despite the use of the excess of Reformatsky reagent, increase of the temperature, and increase of the duration of heating of the reaction mixture.

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E. A. Nikiforova

Perm State National Research University

Author for correspondence.
Email: vikro@ya.ru
ORCID iD: 0000-0002-0871-9154
Russian Federation, ul. Bukireva, 15, Perm, 614990

D. P. Zverev

Perm State National Research University

Email: vikro@ya.ru
ORCID iD: 0000-0002-6060-7678
Russian Federation, ul. Bukireva, 15, Perm, 614990

M. V. Dmitriev

Perm State National Research University

Email: vikro@ya.ru
ORCID iD: 0000-0002-8817-0543
Russian Federation, ul. Bukireva, 15, Perm, 614990

N. F. Kirillov

Perm State National Research University

Email: vikro@ya.ru
ORCID iD: 0000-0001-6149-6829
Russian Federation, ul. Bukireva, 15, Perm, 614990

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6. Figure. General view of the molecule of 1-{(Z)-3-[(E)-3-(2,4-dichlorophenyl)-1-hydroxyallylidene]-2-oxochroman-4-yl}cyclopentanecarboxylate (4e) in thermal ellipsoids of 30% probability according to X-ray diffraction data

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