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

被引:31
作者
Aksenov, Alexander V. [1 ]
Khamraev, Vladislav [1 ]
Aksenov, Nicolai A. [1 ]
Kirilov, Nikita K. [1 ]
Domenyuk, Dmitriy A. [2 ]
Zelensky, Vladimir A. [2 ]
Rubin, Michael [1 ,3 ]
机构
[1] North Caucasus Fed Univ, Dept Chem, 1a Pushkin St, Stavropol 355009, Russia
[2] Stavropol State Med Univ, Dept Gen Practice Dent & Child Dent, 310 Mira St, Stavropol 355017, Russia
[3] Univ Kansas, Dept Chem, 1567 Irving Hill Rd, Lawrence, KS 66045 USA
基金
俄罗斯基础研究基金会;
关键词
ONE-POT SYNTHESIS; BENZOXAZOLES; DESIGN; NITRO;
D O I
10.1039/c9ra00976k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel methodology for general and chemoselective preparation of non-symmetric 1,3,4-oxadiazoles is developed. This unusual reaction proceeds via polyphosphoric acid-assisted activation of nitroalkanes towards nucleophilic attack with acylhydrazides.
引用
收藏
页码:6636 / 6642
页数:7
相关论文
共 34 条
[1]   Electrophilically activated nitroalkanes in the synthesis of 6,7-dihydro-1H-cyclopenta[g]perimidines [J].
Aksenov, A. V. ;
Aksenov, N. A. ;
Ovcharov, D. S. ;
Shcherbakov, S. V. ;
Smirnova, A. N. ;
Aksenova, I. V. ;
Goncharov, V. I. ;
Rubin, M. A. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (07) :1081-1084
[2]   Dual role of polyphosphoric acid-activated nitroalkanes in oxidative peri-annulations: efficient synthesis of 1,3,6,8-tetraazapyrenes [J].
Aksenov, Alexander V. ;
Ovcharov, Dmitrii S. ;
Aksenov, Nicolai A. ;
Aksenov, Dmitrii A. ;
Nadein, Oleg N. ;
Rubin, Michael .
RSC ADVANCES, 2017, 7 (48) :29927-29932
[3]   Rational design of an efficient one-pot synthesis of 6H-pyrrolo[2,3,4-gh] perimidines in polyphosphoric acid [J].
Aksenov, Alexander V. ;
Aksenov, Nicolai A. ;
Ovcharov, Dmitrii S. ;
Aksenov, Dmitrii A. ;
Griaznov, Georgii ;
Voskressensky, Leonid G. ;
Rubin, Michael .
RSC ADVANCES, 2016, 6 (85) :82425-82431
[4]   Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes [J].
Aksenov, Alexander V. ;
Smirnov, Alexander N. ;
Aksenov, Nicolai A. ;
Bijieva, Asiyat S. ;
Aksenova, Inna V. ;
Rubin, Michael .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (14) :4289-4295
[5]   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
[6]   One-pot synthesis of benzoxazoles via the metal-free ortho-C-H functionalization of phenols with nitroalkanes [J].
Aksenov, Nicolai A. ;
Aksenov, Alexander V. ;
Nadein, Oleg N. ;
Aksenov, Dmitrii A. ;
Smirnov, Alexander N. ;
Rubin, Michael .
RSC ADVANCES, 2015, 5 (88) :71620-71626
[7]   Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) [J].
Ballini, R ;
Petrini, M .
TETRAHEDRON, 2004, 60 (05) :1017-1047
[8]   The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation [J].
Ballini, Roberto ;
Petrini, Marino .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (11) :2371-2402
[9]  
Brown BJ, 2000, SYNLETT, P131
[10]   Convenient preparation of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles promoted by Dess-Martin reagent [J].
Dobrota, Cristian ;
Paraschivescu, Codruta C. ;
Dumitru, Ioana ;
Matache, Mihaela ;
Baciu, Ion ;
Ruta, Lavinia L. .
TETRAHEDRON LETTERS, 2009, 50 (17) :1886-1888