Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes

被引:53
作者
Aksenov, Alexander V. [1 ]
Smirnov, Alexander N. [1 ]
Aksenov, Nicolai A. [1 ]
Bijieva, Asiyat S. [1 ]
Aksenova, Inna V. [1 ]
Rubin, Michael [1 ,2 ]
机构
[1] North Caucasus Fed Univ, Dept Chem, Stavropol 355009, Russia
[2] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA
基金
俄罗斯基础研究基金会;
关键词
NON-HODGKINS-LYMPHOMA; 3-SUBSTITUTED; 2-QUINOLONES; BIOLOGICAL EVALUATION; POLYPHOSPHORIC ACID; COMPLEXES; DERIVATIVES; LIGANDS; TELMISARTAN; BENZOTHIAZOLES; ACETAMINATION;
D O I
10.1039/c5ob00131e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:4289 / 4295
页数:7
相关论文
共 56 条
[1]   Palladium-Catalyzed Direct Arylations, Alkenylations, and Benzylations through C-H Bond Cleavages with Sulfamates or Phosphates as Electrophiles [J].
Ackermann, Lutz ;
Barfuesser, Sebastian ;
Pospech, Jola .
ORGANIC LETTERS, 2010, 12 (04) :724-726
[2]   NOVEL METHOD FOR THE ACETAMINATION OF CROWN ETHERS [J].
Aksenov, A. V. ;
Aksenov, N. A. ;
Nadein, O. N. ;
Aksenova, I. V. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 46 (11) :1405-1406
[3]   NEW METHOD FOR THE ACETAMINATION OF PERIMIDINES [J].
Aksenov, A. V. ;
Aksenov, N. A. ;
Nadein, O. N. ;
Tsys, A. E. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (08) :1025-1026
[4]   Metal-free ring expansion of indoles with nitroalkenes: a simple, modular approach to 3-substituted 2-quinolones [J].
Aksenov, Alexander V. ;
Smirnov, Alexander N. ;
Aksenov, Nicolai A. ;
Aksenova, Inna V. ;
Matheny, Jonathon P. ;
Rubin, Michael .
RSC ADVANCES, 2015, 5 (12) :8647-8656
[5]   Highly efficient modular metal-free synthesis of 3-substituted 2-quinolones [J].
Aksenov, Alexander V. ;
Smirnov, Alexander N. ;
Aksenov, Nicolai A. ;
Aksenova, Inna V. ;
Bijieva, Asiyat S. ;
Rubin, Michael .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (48) :9786-9788
[6]   Metal-free transannulation reaction of indoles with nitrostyrenes: a simple practical synthesis of 3-substituted 2-quinolones [J].
Aksenov, Alexander V. ;
Smirnov, Alexander N. ;
Aksenov, Nicolai A. ;
Aksenova, Inna V. ;
Frolova, Liliya V. ;
Kornienko, Alexander ;
Magedov, Igor V. ;
Rubin, Michael .
CHEMICAL COMMUNICATIONS, 2013, 49 (81) :9305-9307
[7]   NITROMETHANE IN POLYPHOSPHORIC ACID-A NEW REAGENT FOR CARBOXYAMIDATION AND CARBOXYLATION OF ACTIVATED AROMATIC COMPOUNDS [J].
Aksenov, Alexander V. ;
Aksenov, Nicolai A. ;
Nadein, Oleg N. ;
Aksenova, Inna V. .
SYNTHETIC COMMUNICATIONS, 2012, 42 (04) :541-547
[8]   Nitroethane in Polyphosphoric Acid: A New Reagent for Acetamidation and Amination of Aromatic Compounds [J].
Aksenov, Alexander V. ;
Aksenov, Nicolai A. ;
Nadein, Oleg N. ;
Aksenova, Inna V. .
SYNLETT, 2010, (17) :2628-2630
[9]   Comparative studies on conventional and microwave synthesis of some benzimidazole, benzothiazole and indole derivatives and testing on inhibition of hyaluronidase [J].
Algul, Oztekin ;
Kaessler, Andre ;
Apcin, Yagmur ;
Yilmaz, Akin ;
Jose, Joachim .
MOLECULES, 2008, 13 (04) :736-748
[10]   Synthesis and biological evaluation of benzo[d]imidazole derivatives as potential anti-cancer agents [J].
Alkahtani, Hamad M. ;
Abbas, Abdullahi Y. ;
Wang, Shudong .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (03) :1317-1321