Acid-Catalyzed Pseudo Five-Component Annulation for a General One-Pot Synthesis of 2,4,6-Triaryl Pyrimidines

被引:18
作者
Ding, Yuxin [1 ,2 ]
Ma, Renchao [1 ]
Hider, Robert C. [3 ]
Ma, Yongmin [1 ,2 ]
机构
[1] Taizhou Univ, Sch Pharmaceut & Chem Engn, Taizhou 318000, Peoples R China
[2] Zhejiang Chinese Med Univ, Sch Pharmaceut Sci, Hangzhou 310053, Peoples R China
[3] Kings Coll London, Inst Pharmaceut Sci, Franklin Wilkins Bldg,Stamford St, London SE1 9NH, England
关键词
2; 4; 6-triaryl pyrimidines; annulation; pseudo five-component reaction; triflic acid; metal-free conditions; 2 DISCRETE NITRILES; SUBSTITUTED PYRIMIDINE; 2+2+2 CYCLOADDITIONS; COORDINATION ARRAYS; MECHANISTIC DETAILS; ANTITUMOR-ACTIVITY; COUPLING REACTIONS; IN-VITRO; DERIVATIVES; DESIGN;
D O I
10.1002/ajoc.201900700
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and general synthesis of 2,4,6-triaryl pyrimidines has been developed. It involves a one-pot [2+1+1+1+1] pseudo five-component annulation of one methyl ketone, two aldehydes and two NH4OAc catalyzed by TfOH. One C-C and four C-N bonds are formed during the oxidative annulation process. The reaction shows good tolerance of many important functional groups in air and produces only water as the coproduct, making this methodology a highly versatile alternative to the existing methods for structuring pyrimidine framework.
引用
收藏
页码:242 / 246
页数:5
相关论文
共 66 条
[1]   Microwave-assisted simple, one-pot, four-component synthesis of 2,4,6-triarylpyrimidines under solvent-free conditions [J].
Adib, Mehdi ;
Mahmoodi, Niusha ;
Mahdavi, Mohammad ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON LETTERS, 2006, 47 (52) :9365-9368
[2]   Synthesis of 2,4,6-trisubstituted pyrimidines as antimalarial agents [J].
Agarwal, A ;
Srivastava, K ;
Puri, SK ;
Chauhan, PMS .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (15) :4645-4650
[3]   Antimalarial activity of 2,4,6-trisubstituted pyrimidines [J].
Agarwal, A ;
Srivastava, K ;
Puri, SK ;
Chauhan, PMS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (07) :1881-1883
[4]   Synthesis of Densely Substituted Pyrimidine Derivatives [J].
Ahmad, Omar K. ;
Hill, Matthew D. ;
Movassaghi, Mohammad .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8460-8463
[5]   Thieno[2,3-d] pyrimidine as a promising scaffold in medicinal chemistry: Recent advances [J].
Ali, Eslam M. H. ;
Abdel-Maksoud, Mohammed S. ;
Oh, Chang-Hyun .
BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (07) :1159-1194
[6]   Inverse Electron Demand Diels-Alder Reactions of 1,2,3-Triazines: Pronounced Substituent Effects on Reactivity and Cycloaddition Scope [J].
Anderson, Erin D. ;
Boger, Dale L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (31) :12285-12292
[7]   Secondary amines immobilized inside magnetic mesoporous materials as a recyclable basic and oxidative heterogeneous nanocatalyst for the synthesis of trisubstituted pyrimidine derivatives [J].
Aryan, Reza ;
Beyzaei, Hamid ;
Nojavan, Masoomeh ;
Dianatipour, Tahereh .
RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (05) :4417-4431
[8]   Designed self-generation of an extended helical structure from an achiral polyheterocyclic strand [J].
Bassani, DM ;
Lehn, JM ;
Baum, G ;
Fenske, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (17) :1845-1847
[9]   Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles [J].
Botella, L ;
Nájera, C .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 663 (1-2) :46-57
[10]   Transition-metal-free selective pyrimidines and pyridines formation from aromatic ketones, aldehydes and ammonium salts [J].
Chen, Jinjin ;
Meng, Huanxin ;
Zhang, Feng ;
Xiao, Fuhong ;
Deng, Guo-Jun .
GREEN CHEMISTRY, 2019, 21 (19) :5201-5206