Direct Catalytic Symmetrical, Unsymmetrical N,N-Dialkylation and Cyclization of Acylhydrazides Using Alcohols

被引:35
作者
Thiyagarajan, Subramanian [1 ]
Gunanathan, Chidambaram [1 ]
机构
[1] HBNI, Natl Inst Sci Educ & Res NISER, Sch Chem Sci, Bhubaneswar 752050, India
关键词
BORROWING HYDROGEN; SECONDARY ALCOHOLS; N-ALKYLATION; C-H; AMINES; DERIVATIVES; HYDRAZIDES; EFFICIENT; POTENT; AMINATION;
D O I
10.1021/acs.orglett.0c02369
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, direct N,N-dialkylation of acylhydrazides using alcohols is reported. This catalytic protocol provides one-pot synthesis of both symmetrical and unsymmetrical N,N-disubstituted acylhydrazides using an assortment of primary and secondary alcohols with remarkable selectivity and excellent yields. Interestingly, the use of diols resulted in intermolecular cyclization of acylhydrazides, and such products are privileged structures in biologically active compounds. Water is the only byproduct, which makes this catalytic protocol sustainable and environmentally benign.
引用
收藏
页码:6617 / 6622
页数:6
相关论文
共 64 条
[1]   Study of Precatalyst Degradation Leading to the Discovery of a New Ru0 Precatalyst for Hydrogenation and Dehydrogenation [J].
Anaby, Aviel ;
Schelwies, Mathias ;
Schwaben, Jonas ;
Rominger, Frank ;
Hashmi, A. Stephen K. ;
Schaub, Thomas .
ORGANOMETALLICS, 2018, 37 (13) :2193-2201
[2]   The Catalytic Amination of Alcohols [J].
Baehn, Sebastian ;
Imm, Sebastian ;
Neubert, Lorenz ;
Zhang, Min ;
Neumann, Helfried ;
Beller, Matthias .
CHEMCATCHEM, 2011, 3 (12) :1853-1864
[3]   Catalytic Conversion of Nonfood Woody Biomass Solids to Organic Liquids [J].
Barta, Katalin ;
Ford, Peter C. .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1503-1512
[4]  
Blumenfeld M., 2011, Improvements Relating to Fabric Treatment Compositions, Patent No. [WO 2009065893, 2009065893]
[5]   A Base and Solvent-Free Ruthenium-Catalyzed Alkylation of Amines [J].
Celaje, Jeff Joseph A. ;
Zhang, Xingyue ;
Zhang, Forrest ;
Kam, Lisa ;
Herron, Jessica R. ;
Williams, Travis J. .
ACS CATALYSIS, 2017, 7 (02) :1136-1142
[6]   The ruthenium-catalysed selective synthesis of mono-deuterated terminal alkynes [J].
Chatterjee, Basujit ;
Gunanathan, Chidambaram .
CHEMICAL COMMUNICATIONS, 2016, 52 (24) :4509-4512
[7]   Ruthenium Catalyzed Selective α- and α,β-Deuteration of Alcohols Using D2O [J].
Chatterjee, Basujit ;
Gunanathan, Chidambaram .
ORGANIC LETTERS, 2015, 17 (19) :4794-4797
[8]   Ruthenium and osmium complexes in C-C bond-forming reactions by borrowing hydrogen catalysis [J].
Chelucci, Giorgio .
COORDINATION CHEMISTRY REVIEWS, 2017, 331 :1-36
[9]   Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis [J].
Corma, Avelino ;
Navas, Javier ;
Sabater, Maria J. .
CHEMICAL REVIEWS, 2018, 118 (04) :1410-1459
[10]   Homogeneous Transition Metal Catalysis of Acceptorless Dehydrogenative Alcohol Oxidation: Applications in Hydrogen Storage and to Heterocycle Synthesis [J].
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2017, 117 (13) :9228-9246