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

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Somente assinantes

Resumo

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.

Sobre autores

E. Nikiforova

Perm State National Research University

Autor responsável pela correspondência
Email: vikro@ya.ru
ORCID ID: 0000-0002-0871-9154
Rússia, ul. Bukireva, 15, Perm, 614990

D. Zverev

Perm State National Research University

Email: vikro@ya.ru
ORCID ID: 0000-0002-6060-7678
Rússia, ul. Bukireva, 15, Perm, 614990

M. Dmitriev

Perm State National Research University

Email: vikro@ya.ru
ORCID ID: 0000-0002-8817-0543
Rússia, ul. Bukireva, 15, Perm, 614990

N. Kirillov

Perm State National Research University

Email: vikro@ya.ru
ORCID ID: 0000-0001-6149-6829
Rússia, ul. Bukireva, 15, Perm, 614990

Bibliografia

  1. Кириллов Н.Ф., Гаврилов А.Г. ЖОХ. 2008, 78, 1189–1191. [Kirillov N.F., Gavrilov A.G. Russ. J. Gen. Chem. 2008, 78, 1422–1424.] doi: 10.1134/S1070363208070244
  2. Кириллов Н.Ф., Гаврилов А.Г. ЖОрХ. 2008, 44, 975–976. [Kirillov N.F., Gavrilov A.G. Russ. J. Org. Chem. 2008, 44, 963–964.] doi: 10.1134/S1070428008070051
  3. Кириллов Н.Ф., Махмудов Р.Р., Гаврилов А.Г., Марданова Л.Г., Вахрин М.И. Хим. фарм. ж. 2013, 47, 41–42. [Kirillov N.F., Makhmudov R.R., Gavrilov A.G., Mardanova L.G., Vakhrin M.I. Pharm. Chem. J. 2013, 47, 40–41.] doi: 10.1007/s11094–013–0892–7
  4. Щепин В.В., Кириллов Н.Ф., Вахрин М.И. ЖОХ. 2006, 76, 1194–1197. [Shchepin V.V., Kirillov N.F., Vakhrin M.I., Bayanova O.B., Shurov S.N., Silaichev P.S. Russ. J. Gen. Chem. 2006, 76, 1146–1149.] doi: 10.1134/S1070363206070255
  5. Кириллов Н.Ф., Никифорова Е.А., Байбародс-ких Д.В. ЖОрХ. 2015, 51, 535–538. [Nikiforova E.A., Kirillov N.F., Baybarodskikh D.V. Russ. J. Org. Chem. 2015, 51, 518–521.] doi: 10.1134/S1070428015040090
  6. Кириллов Н.Ф., Никифорова Е.А., Дмитриев М.В., Байбародских Д.В. ЖСХ. 2016, 57, 1327–1329. [Kirillov N.F., Nikiforova E.A., Dmitriev M.V., Baibarodskikh D.V. J. Struct. Chem. 2016, 57, 1263–1265.] doi: 10.1134/S0022476616060275
  7. Щепин В.В., Кириллов Н.Ф., Вахрин М.И. ЖОрХ. 2007, 43, 1549–1551. [Shchepin V.V., Kirillov N.F., Vakhrin M.I., Bayanova O.B., Shurov S.N. Russ. J. Org. Chem. 2007, 43, 1545–1547.] doi: 10.1134/S1070428007100235
  8. Никифорова Е.А., Кириллов Н.Ф., Байбародс-ких Д.В. ЖОрХ. 2019, 55, 1304–1306. [Nikiforova E.A., Kirillov N.F., Baibarodskikh D.V. Russ. J. Org. Chem. 2019, 55, 1244–1245. doi: 10.1134/S1070428019080281]
  9. Щепин В.В., Калюжный М.М., Русских Н.Ю. ХГС. 2004, 40, 1108–1109. [Shchepin V.V., Kalyugnii M.M., Russkikh N.Y. Chem. Heterocycl. Compd. 2004, 40, 956–957.] doi: 10.1023/B: COHC.0000044582.88939.04
  10. Никифорова Е.А., Махмудов Р.Р., Рудин А.А., Дмит-риев М.В., Байбародских Д.В., Кириллов Н.Ф., Зверев Д.П., Романов А.М. ЖОХ. 2021, 91, 76–84. [Nikiforova E.A., Makhmudov R.R., Rudin A.A., Dmitriev M.V., Baibarodskikh D.V., Kirillov N.F., Zve-rev D.P., Romanov A.M. Russ. J. Gen. Chem. 2021, 91, 64–71.] doi: 10.1134/S1070363221010060
  11. Кириллов Н.Ф., Никифорова Е.А., Васянин А.Н., Дмитриев М.В. ЖОрХ. 2015, 51, 530–534. [Kirillov N.F., Nikiforova E.A., Vasyanin A.N., Dmit-riev M.V. Russ. J. Org. Chem. 2015, 51, 513–517.] doi: 10.1134/S1070428015040089
  12. Щепин В.В., Кириллов Н.Ф., Вахрин М.И. ЖОрХ. 2004, 74, 1009–1012. [Shchepin V.V., Kirillov N.F., Vakhrin M.I. 2004, 74, 933–936.] doi: 10.1023/B: RUGC.0000042430.44366.01
  13. CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27–03–2014 CrysAlis171.NET).
  14. Palatinus L., Chapuis G.J. Appl. Crystallogr. 2007, 40, 786–790. doi: 10.1107/s0021889807029238
  15. Sheldrick G.M. Acta Crystallogr., Sect. C: Structur. Chem. 2015, 71, 3–8. doi: 10.1107/S2053229614024218
  16. Dolomanov O.V., Bourhis L.J., Gildea R.J., Ho-ward J.A.K., Puschmann H.J. Appl. Crystallogr. 2009, 42, 339–341. doi: 10.1107/s0021889808042726
  17. Beilsteins Handbuch der organischen Chemie, 4th ed., vol. 9, p. 9.
  18. Čačić M., Molnar M., Strelec I. Heterocycles. 2011, 83, 1553–1566. doi: 10.3987/com-11–12196

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar

Declaração de direitos autorais © Russian Academy of Sciences, 2024