Transition-Metal-Free [3+2] Cycloaddition of Nitroolefins and Diazoacetonitrile: A Facile Access to Multisubstituted Cyanopyrazoles

被引：50
作者：
Chen, Zhen
Zhang, Yue
Nie, Jing
Ma, Jun-An [1 ]
机构：
[1] Tianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 07期
基金：
中国国家自然科学基金;
关键词：
IN-SITU GENERATION; PALLADIUM-CATALYZED CYANATION; BESTMANN-OHIRA REAGENT; TRIFLUOROMETHYL DIAZOMETHANE; REGIOSELECTIVE SYNTHESIS; DIFLUOROMETHYL DIAZOMETHANE; DERIVATIVES; NITRILES; ALKYNES; FLOW;
D O I：
10.1021/acs.orglett.8b00729
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A transition-metal-free [3 + 2] cycloaddition reaction between nitroolefins and diazoacetonitrile (N2CHCN) is described. This protocol exhibits several merits including simple starting materials, mild reaction conditions, broad substrate scope, good yields, and regioselectivities. The one-pot three-component reaction of nitroolefins with diazoacetonitrile (N2CHCN) and alkyl halides is also developed, thus delivering a series of multisubstituted cyanopyrazoles in good to high yields.
引用
收藏
页码：2120 / 2124
页数：5
相关论文
共 81 条
[1]   Synthesis and Applications of α-Trifluoromethylated Alkylboron Compounds [J].
Argintaru, O. Andreea ;
Ryu, DaWeon ;
Aron, Ioana ;
Molander, Gary A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (51) :13656-13660
[2]   Synthesis of Trifluoromethyl-Substituted 3-Azabicyclo[n.1.0]alkanes: Advanced Building Blocks for Drug Discovery [J].
Artamonov, Olexiy S. ;
Slobodyanyuk, Evgeniy Y. ;
Volochnyuk, Dmitriy M. ;
Komarov, Igor V. ;
Tolmachev, Andrey A. ;
Mykhailiuk, Pavel K. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) :3592-3598
[3]   Synthesis of Isomeric 6-Trifluoromethyl-3-azabicyclo[3.1.0]hexanes: Conformationally Restricted Analogues of 4-Trifluoromethylpiperidine [J].
Artamonov, Olexiy S. ;
Slobodyanyuk, Evgeniy Y. ;
Shishkin, Oleg V. ;
Komarov, Igor V. ;
Mykhailiuk, Pavel K. .
SYNTHESIS-STUTTGART, 2013, 45 (02) :225-230
[4]   Batch and Continuous-Flow One-Pot Processes using Amine Diazotization to Produce Silylated Diazo Reagents [J].
Audubert, Clement ;
Marin, Oscar Javier Gamboa ;
Lebel, Helene .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (22) :6294-6297
[5]   A Unified Continuous Flow Assembly-Line Synthesis of Highly Substituted Pyrazoles and Pyrazolines [J].
Britton, Joshua ;
Jamison, Timothy F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (30) :8823-8827
[6]   A Homogeneous Method for the Conveniently Scalable Palladium- and Nickel-Catalyzed Cyanation of Aryl Halides [J].
Burg, Finn ;
Egger, Julian ;
Deutsch, Johannes ;
Guimond, Nicolas .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (08) :1540-1545
[7]   Phenylpyrazole insecticide photochemistry, metabolism, and GABAergic action: Ethiprole compared with fipronil [J].
Caboni, P ;
Sammelson, RE ;
Casida, JE .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (24) :7055-7061
[8]   Chiral Bronsted acid-catalyzed diastereo- and enantioselective synthesis of CF3-substituted aziridines [J].
Chai, Zhuo ;
Bouillon, Jean-Philippe ;
Cahard, Dominique .
CHEMICAL COMMUNICATIONS, 2012, 48 (76) :9471-9473
[9]   Use of a Traceless Activating and Directing Group for the Construction of Trifluoromethylpyrazoles: One-Pot Transformation of Nitroolefins and Trifluorodiazoethane [J].
Chen, Zhen ;
Zheng, Yan ;
Ma, Jun-An .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (16) :4569-4574
[10]   Mild Palladium-Catalyzed Cyanation of (Hetero)aryl Halides and Triflates in Aqueous Media [J].
Cohen, Daniel T. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2015, 17 (02) :202-205
123456789