Reaction of 2-aminobenzoimidazoles with acetylene in the KOBut /DMSO system: self-organization of benzo[d]-imidazo[1,2-a]imidazoles and benzo[4,5]imidazo[1,2-a]-pyrimidines by the competition of nucleophilic centers

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2-Aminobenzoimidazoles react with acetylene in the KOBut/DMSO superbase system (80°С, 20 min) to give benzoimidazo[1,2-a]imidazoles and benzoimidazo[1,2-a]pyrimidines, the products of self-organization of starting compounds with two or three molecules of acetylene. Moreover, vinyl derivatives of 1,3-dihydro-2H-benzo[d]imidazole-2-imine were obtained.

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作者简介

N. Semenova

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: boris_trofimov@irioch.irk.ru
ORCID iD: 0000-0002-2937-970X
俄罗斯联邦, ul. Favorskogo, 1, Irkutsk, 664033

I. Ushakov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: boris_trofimov@irioch.irk.ru
ORCID iD: 0000-0003-0176-1699
俄罗斯联邦, ul. Favorskogo, 1, Irkutsk, 664033

E. Schmidt

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences; Angarsk State Technical University

Email: boris_trofimov@irioch.irk.ru
ORCID iD: 0000-0002-0188-3015
俄罗斯联邦, ul. Favorskogo, 1, Irkutsk, 664033; ul. Tchaikovskogo, 60, Angarsk, 665835

B. Trofimov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

编辑信件的主要联系方式.
Email: boris_trofimov@irioch.irk.ru
ORCID iD: 0000-0002-0430-3215
俄罗斯联邦, ul. Favorskogo, 1, Irkutsk, 664033

参考

  1. Trofimov B.A., Schmidt E.Yu. Acc. Chem. Res. 2018, 51, 1117–1130. doi: 10.1021/acs.accounts.7b00618
  2. Шмидт Е.Ю., Трофимов Б.А. Докл. РАН. Химия, науки о материалах. 2022, 505, 5–24. [Schmidt E.Yu., Trofimov B.A. Doklady Chemistry. 2022, 505, 127–145.] doi: 10.1134/S0012500822700069
  3. Semenova N.V., Ivanova E.V., Bidusenko I.A., Trofimov B.A. Mendeleev Commun. 2020, 30, 109–111. doi: 10.1016/j.mencom.2020.01.036
  4. Schmidt E.Yu., Semenova N.V., Ushakov I.A., Vashchenko A.V., Trofimov B.A. Org. Lett. 2021, 23, 4743–4748. doi: 10.1021/acs.orglett.1c01460
  5. Semenova N.V., Schmidt E.Yu., Ushakov I.A., Trofimov B.A. Mendeleev. Commun. 2023, 33, 164–166. doi: 10.1016/j.mencom.2023.02.005
  6. Bidusenko I.A., Schmidt E.Yu., Ushakov I.A., Trofimov B.A. Eur. J. Org. Chem. 2018, 2018, 4845–4849. doi: 10.1002/ejoc.201800850
  7. Байкалова Л.В., Домнина Е.С., Афонин А.В. Изв. АН. Сер. Хим. 1992, 3, 749–751. [Baikalova L.V., Domnina E.S., Afonin A.V. Russ. Chem. Bull. 1992, 41, 588–589.] doi: 10.1007/BF00863093
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