Synthesis of 2,3-Dihydrobenzo[B][1,4]Dioxins by the Hetero-Diels-Alder Reaction Based on 3,5-Di(tert-butyl)-6-nitro-1,2-benzoquinone

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 订阅存取

详细

A sterically hindered o-quinone activated by a nitro group can act as an effective diene in the Diels-Alder reaction. The interaction of a twofold excess of 3,5-di-(tert-butyl)-6-nitro-1,2-benzoquinone in the reaction with arylamines in an isopropanol/methylethyl ketone medium (1 : 1) leads to the formation of derivatives ((2,3-dihydrobenzo[ b][1,4]dioxin-2-yl)oxy)-3-nitrophenols.

全文:

受限制的访问

作者简介

E. Ivakhnenko

Southern Federal University

编辑信件的主要联系方式.
Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0003-0338-6466
俄罗斯联邦, Rostov-on-Don

V. Malay

North Caucasus Federal University

Email: malay@sfedu.ru
ORCID iD: 0000-0002-5302-743X
俄罗斯联邦, Stavropol

O. Demidov

North Caucasus Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0002-3586-0487
俄罗斯联邦, Stavropol

N. Merezhko

Southern Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0009-0000-2672-4072
俄罗斯联邦, Rostov-on-Don

S. Kislitsin

Southern Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0009-0007-0873-696X
俄罗斯联邦, Rostov-on-Don

V. Minkin

Southern Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0001-6096-503X
俄罗斯联邦, Rostov-on-Don

参考

  1. Abakumov G.A., Druzhkov N.O., Kurskii Yu.A., Abakumova L.G., Shavyrin F.S., Fukin G.A. Russ Chem Bull., 2005, 54, 2571–2577. doi: 10.1007/s11172-0157-7
  2. Vasu D., Leich J.A., Dixon D.J. Tetrahedron, 2019, 75, 50, 130726. doi: 10.1016/j.tet.2019.130726
  3. Nicolas Y., Allama F., Lepeltier M., Massin J., Castet F., Ducasse L., Hirsch I., Boubegtiten Z., Jonusauskas G., Olivier C., Toupance T.. Chem Eur J. 2014, 20, 3678–88. doi 10.1002/ chem.201303775
  4. Ivakhnenko E., Malay V., Romanenko G., Demidov O., Knyazev P., Starikov A., Minkin V. Tetrahedron 2021, 79, 131841. doi: 10.1016/j.tet.2020.131841
  5. Ивахненко Е.П., Малай В.И., Демидов О.П., Минкин В.И. ЖОрХ. 2023, 59, 8, 1032–1040. doi: 10.31857/S0514749223080049
  6. Ivakhnenko E., Malay V., Demidov O., Starikov A., Min-kin V. Tetrahedron 2022, 103, 132575. doi: 10.1016/j.tet.2021.132575
  7. Hernandez-Juan F.A., Cockfield D.M., Dixon D.J. Tetrahedron Lett. 2007, 48, 1605-1608. doi: 10.1016/j/tetlet.2006.12.140
  8. Richard A.S. , Murthy S.M., Basavaraju Y.B., Yathirajan H.S., Parkin S., Van Meervelt L. Acta Crystallographica, E. Cryst. Com. 2023, 79, 674-677. doi: 10.1107/S2056989023005613
  9. Mazza S., Danishefsky S., McCurry P. J. Org. Chem. 1976, 39, 3610–3611. doi: 10.1021/jo00938a043.
  10. Charini R., Fang C., Herrington D., Higgs K., Rodrigo R., Taylor N. Aust. J. Chem. 1997, 50, 271–278. doi. 10.1071/C96099
  11. Escorihuela J., Looijen W., Wang X., Aquino A., Lischka H., Zuilhof H. J. Org. Chem. 2020, 85, 13557–13566. doi: 10.1021/acs.joc.0c01674
  12. Bekele T., Shah M. H., Wolfer J., Abraham C. J., Weatherwax A, Lectka T. J. Am. Chem. Soc. 2006, 128, 1810–1811. doi: 10.1021/ja058077g

补充文件

附件文件
动作
1. JATS XML
下载
2. Scheme 1. Synthesis of 6-(tert-butyl)-2-methyl-1-aryl-1H-cyclopenta[b]pyridine-4,5-diones 2

下载 (35KB)
索引源数据
3. Scheme 2. Synthesis of dihydrobenzo[b][1,4]dioxin-2-yl-oxy-3-nitrophenols 4

下载 (80KB)
索引源数据
4. Fig. 1. Molecular structure of compounds 4 (c)

下载 (110KB)
索引源数据
5. Fig. 2. Side view in two projections of dioxin fragment 4 (c). Hydrogen atoms are omitted for clarity

下载 (103KB)
索引源数据

版权所有 © Russian Academy of Sciences, 2024