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

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅或者付费存取

详细

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.

全文:

受限制的访问

作者简介

E. Nikiforova

Perm State National Research University

编辑信件的主要联系方式.
Email: vikro@ya.ru
ORCID iD: 0000-0002-0871-9154
俄罗斯联邦, ul. Bukireva, 15, Perm, 614990

D. Zverev

Perm State National Research University

Email: vikro@ya.ru
ORCID iD: 0000-0002-6060-7678
俄罗斯联邦, ul. Bukireva, 15, Perm, 614990

M. Dmitriev

Perm State National Research University

Email: vikro@ya.ru
ORCID iD: 0000-0002-8817-0543
俄罗斯联邦, ul. Bukireva, 15, Perm, 614990

N. Kirillov

Perm State National Research University

Email: vikro@ya.ru
ORCID iD: 0000-0001-6149-6829
俄罗斯联邦, ul. Bukireva, 15, Perm, 614990

参考

  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

补充文件

附件文件
动作
1. JATS XML
下载
2. Scheme 1

下载 (188KB)
索引源数据
3. Scheme 2

下载 (169KB)
索引源数据
4. Scheme 3

下载 (68KB)
索引源数据
5. Scheme 4

下载 (138KB)
索引源数据
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

下载 (241KB)
索引源数据
7. Figure from Contents

下载 (97KB)
索引源数据

版权所有 © Russian Academy of Sciences, 2024