Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes

Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes

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

Сохранить в:

Библиографические подробности
Главные авторы:	Aksenov, A. V., Аксенов, А. В., Smirnov, A. N., Смирнов, А. Н., Aksenov, N. A., Аксенов, Н. А., Bijieva, A. S., Биджиева, А. С., Aksenova, I. V., Аксенова, И. В., Rubin, M. A., Рубин, М. А.
Формат:	Статья
Язык:	English
Опубликовано:	Royal Society of Chemistry 2018
Темы:	Addition reaction Aniline Benzimidazole Benzoxazoles Cyclocondensation Nitroalkanes Nucleophilic addition Umpolung
Online-ссылка:	https://dspace.ncfu.ru/handle/20.500.12258/3722
Метки:	Добавить метку Нет меток, Требуется 1-ая метка записи!

Схожие документы

Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?
Автор: Aksenov, A. V., и др.
Опубликовано: (2021)

Directed nucleophilic addition of phenoxides to cyclopropenes
Автор: Aksenov, N. A., и др.
Опубликовано: (2018)

One-pot synthesis of benzoxazoles via the metal-free ortho-C-H functionalization of phenols with nitroalkanes
Автор: Aksenov, N. A., и др.
Опубликовано: (2018)

Intramolecular nucleophilic addition of carbanions generated from: N -benzylamides to cyclopropenes
Автор: Aksenov, N. A., и др.
Опубликовано: (2018)

Unexpected cyclization ortho-nitrochalcones into 2-alkylideneindolin-3-ones
Автор: Aksenov, N. A., и др.
Опубликовано: (2020)

Michael addition to unprotected 3-(2-nitrovinyl)indoles under the conditions of microwave synthesis
Автор: Aksenov, A. V., и др.
Опубликовано: (2018)

Michael addition to 3-(2-nitrovinyl)indoles – route toward aliphatic nitro compounds with heterocyclic substituents
Автор: Aksenov, N. A., и др.
Опубликовано: (2019)

Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence
Автор: Aksenov, A. V., и др.
Опубликовано: (2021)

Electrophilically activated nitroalkanes in reaction with aliphatic diamines en route to imidazolines
Автор: Aksenov, A. V., и др.
Опубликовано: (2019)

Oxidative Cyclization of 4-(2-Aminophenyl)-4-oxo-2-phenylbutanenitriles into 2-(3-Oxoindolin-2-ylidene)acetonitriles
Автор: Aksenov, N. A., и др.
Опубликовано: (2022)

Determination of the Solubility Limit of Ruthenium Ions in the Structure of Yttrium Aluminum Garnet
Автор: Suprunchuk, V. E., и др.
Опубликовано: (2025)

A novel method for the synthesis of 2-arylquinolin-4(1H)-ones
Автор: Arutiunov, N. A., и др.
Опубликовано: (2024)

Recent advances in chemistry of β-cyano ketones
Автор: Aksenov, N. A., и др.
Опубликовано: (2025)

Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines
Автор: Aksenov, A. V., и др.
Опубликовано: (2019)

Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal SN2′ Substitution of Bromocylopropanes
Автор: Rubina, M. Y., и др.
Опубликовано: (2022)

Influence of the MgO/CaO Sintering Additive Ratio on the Optical Properties of YAG:Cr Ceramics
Автор: Kravtsov, A. A., и др.
Опубликовано: (2025)

New 6'-Amino-5'-cyano-2-oxo-1,2-dihydro-1'H-spiro[indole-3,4'-pyridine]-3'-carboxamides: Synthesis, Reactions, Molecular Docking Studies and Biological Activity
Автор: Dotsenko, V. V., и др.
Опубликовано: (2023)

Microwave synthesis of 2-[(E)-2-(1H-indol-3-yl)vinyl]hetarenes
Автор: Aksenov, A. V., и др.
Опубликовано: (2018)

Direct metal-free synthesis of diarylamines from 2-nitropropane via the twofold C-H functionalization of arenes
Автор: Aksenov, A. V., и др.
Опубликовано: (2019)

Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies
Автор: Dotsenko, V. V., и др.
Опубликовано: (2023)

Preparation of YAG:Ce Ceramics with High Luminescent Properties
Автор: Lapin, V. A., и др.
Опубликовано: (2025)

Synthesis of New 2,2':6',2''-Terpyridin Series with Directly Linked Benzimidazole Moieties
Автор: Demidov, O. P., и др.
Опубликовано: (2025)

One-pot synthesis of substituted quinolines and 3,3′-(arylmethylene)bis(1H-indoles) via a metal-free polyphosphoric acid-mediated acetylene hydrolysis strategy
Автор: Arutiunov, N. A., и др.
Опубликовано: (2025)

Reaction of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Hydroxycyclohexanones
Автор: Dotsenko, V. V., и др.
Опубликовано: (2019)

A facile approach to the synthesis of 3,4-dihydro-2H-benzo[4,5]imidazo[2,1-b][1,3,4]thiadiazines
Автор: Pobedinskaya, D. Y., и др.
Опубликовано: (2024)

Synthesis of 3,4-dihydroisoquinolines using nitroalkanes in polyphosphoric acid
Автор: Aksenov, N. A., и др.
Опубликовано: (2019)

Direct C-H functionalization of arenes in reactions with nitroalkanes and nitroalkenes in polyphosphoric acids
Автор: Aksenov, A. V., и др.
Опубликовано: (2019)

Influence of MgO and CaO sintering additives on thermophysical, luminescent and optical properties of LuAG: Yb3+ laser ceramics
Автор: Lapin, V. A., и др.
Опубликовано: (2024)

Synthesis of 2,4-Disubstituted Quinolines by the Reaction of Propargylic Alcohols with Anilines in a Polyphosphoric Acid Medium
Автор: Aksenov, A. V., и др.
Опубликовано: (2025)

Substitution of Praseodymium for Cadmium and Lead in the Structure of Pr5Mo3O16+δ
Автор: Berezhnaya, T. S., и др.
Опубликовано: (2025)

Electrophilically activated nitroalkanes in synthesis of 3,4-dihydroquinozalines
Автор: Aksenov, A. V., и др.
Опубликовано: (2021)

Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity
Автор: Aksenov, N. A., и др.
Опубликовано: (2020)

Electrophilically activated nitroalkanes in the synthesis of substituted 1,3,4-oxadiazoles from amino acid derivatives
Автор: Aksenov, A. V., и др.
Опубликовано: (2022)

Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles
Автор: Aksenov, A. V., и др.
Опубликовано: (2019)

Electrophilically activated nitroalkanes in double annulation of [1,2,4]triazolo[4,3-a]quinolines and 1,3,4-oxadiazole rings
Автор: Aksenov, A. V., и др.
Опубликовано: (2021)

Preparation of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles via chemoselective сyclocondensation of electrophilically activated nitroalkanes to (thio)semicarbazides or thiohydrazides
Автор: Aksenov, N. A., и др.
Опубликовано: (2020)

Dual role of polyphosphoric acid-activated nitroalkanes in oxidative peri -annulations: Efficient synthesis of 1,3,6,8-tetraazapyrenes
Автор: Aksenov, A. V., и др.
Опубликовано: (2018)

Correction: Directed nucleophilic addition of phenoxides to cyclopropenes (Organic and biomolecular chemistry (2018) 16 (5719) DOI: 10.1039/C7OB01785E)
Автор: Aksenov, N. A., и др.
Опубликовано: (2018)

One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes
Автор: Grishin, I. Y., и др.
Опубликовано: (2025)

Electrophilically activated nitroalkanes in the synthesis of 6,7-dihydro-1H-cyclopenta[g]perimidines
Автор: Aksenov, A. V., и др.
Опубликовано: (2018)