Literature DB >> 25758157

Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes.

Alexander V Aksenov1, Alexander N Smirnov, Nicolai A Aksenov, Asiyat S Bijieva, Inna V Aksenova, Michael Rubin.   

Abstract

PPA-induced umpolung triggers efficient nucleophilic addition of unactivated anilines to nitroalkanes to produce N-hydroxyimidamides. The latter undergo sequential acid-promoted cyclocondensation with ortho-OH or ortho-NHR moieties to afford benzoxazoles and benzimidazoles, respectively.

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Year:  2015        PMID： 25758157     DOI： 10.1039/c5ob00131e

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  9 in total

1.  Electrophilically activated nitroalkanes in reaction with aliphatic diamines en route to imidazolines.

Authors:  Alexander V Aksenov; Nicolai A Aksenov; Nikolai A Arutiunov; Vladimir V Malyuga; Sergey N Ovcharov; Michael Rubin
Journal:  RSC Adv       Date:  2019-11-29       Impact factor: 4.036

2.  Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?

Authors:  Alexander V Aksenov; Nicolai A Aksenov; Nikita K Kirilov; Anton A Skomorokhov; Dmitrii A Aksenov; Igor A Kurenkov; Elena A Sorokina; Mezvah A Nobi; Michael Rubin
Journal:  RSC Adv       Date:  2021-11-04       Impact factor: 4.036

3.  Copper(II)-Dioxygen Facilitated Activation of Nitromethane: Nitrogen Donors for the Synthesis of Substituted 2-Hydroxyimino-2-phenylacetonitriles and Phthalimides.

Authors:  Shiqun Xiang; Yinghua Li; Weibin Fan; Jiang Jin; Wei Zhang; Deguang Huang
Journal:  Front Chem       Date:  2021-01-29       Impact factor: 5.221

4.  Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes.

Authors:  Dmitrii A Aksenov; Nikolai A Arutiunov; Vladimir V Maliuga; Alexander V Aksenov; Michael Rubin
Journal:  Beilstein J Org Chem       Date:  2020-11-26       Impact factor: 2.883

5.  A convenient one-pot synthesis of N-substituted amidoximes and their application toward 1,2,4-oxadiazol-5-ones.

Authors:  Wong Phakhodee; Chuthamat Duangkamol; Nitaya Wiriya; Mookda Pattarawarapan
Journal:  RSC Adv       Date:  2018-11-14       Impact factor: 4.036

6.  A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities.

Authors:  Nicolai A Aksenov; Alexander V Aksenov; Alexander Kornienko; Annelise De Carvalho; Véronique Mathieu; Dmitrii A Aksenov; Sergei N Ovcharov; Georgii D Griaznov; Michael Rubin
Journal:  RSC Adv       Date:  2018-11-01       Impact factor: 3.361

7.  Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles.

Authors:  Alexander V Aksenov; Vladislav Khamraev; Nicolai A Aksenov; Nikita K Kirilov; Dmitriy A Domenyuk; Vladimir A Zelensky; Michael Rubin
Journal:  RSC Adv       Date:  2019-02-26       Impact factor: 3.361

8.  Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines.

Authors:  Stanislav S Shcherbakov; Artyom Yu Magometov; Viktoriia Yu Shcherbakova; Alexander V Aksenov; Dmitriy A Domenyuk; Vladimir A Zelensky; Michael Rubin
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 3.361

9.  Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity.

Authors:  Nicolai A Aksenov; Alexander V Aksenov; Nikita K Kirilov; Nikolai A Arutiunov; Dmitrii A Aksenov; Vladimir Maslivetc; Zhenze Zhao; Liqin Du; Michael Rubin; Alexander Kornienko
Journal:  Org Biomol Chem       Date:  2020-08-19       Impact factor: 3.876
  9 in total

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