Acceptorless dehydrogenative synthesis of 2-substituted quinazolines from 2-aminobenzylamine with primary alcohols or aldehydes by heterogeneous Pt catalysts

被引:32
作者
Chaudhari, Chandan [1 ]
Siddiki, S. M. A. Hakim [2 ]
Tamura, Masazumi [3 ]
Shimizu, Ken-ichi [1 ,2 ]
机构
[1] Hokkaido Univ, Catalysis Res Ctr, Sapporo, Hokkaido 0010021, Japan
[2] Kyoto Univ, Elements Strategy Initiat Catalysts & Batteries, Katsura, Kyoto 6158520, Japan
[3] Tohoku Univ, Sch Engn, Dept Appl Chem, Aoba Ku, Sendai, Miyagi 9808579, Japan
关键词
SUPPORT; OXIDANT;
D O I
10.1039/c4ra09205h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
CeO2-supported Pt nanoparticle catalysts enabled the acceptorless dehydrogenative synthesis of 2-substituted quinazolines from 2-aminobenzylamine with aliphatic and benzyl primary alcohols or aldehydes with low catalyst loading, wide substrate scope and good catalyst reusability, demonstrating the first acceptor-free and additive-free catalytic system for this reaction.
引用
收藏
页码:53374 / 53379
页数:6
相关论文
共 21 条
[1]   Synthesis and biological activity of novel antibacterial quinazolines [J].
Bedi, PMS ;
Kumar, V ;
Mahajan, MP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (20) :5211-5213
[2]   Dual kinase inhibition in the treatment of breast cancer: Initial experience with the EGFR/ErbB-2 inhibitor lapatinib [J].
Burris, HA .
ONCOLOGIST, 2004, 9 :10-15
[3]   C-3 alkylation of oxindole with alcohols by Pt/CeO2 catalyst in additive-free conditions [J].
Chaudhari, Chandan ;
Siddiki, S. M. A. Hakim ;
Kon, Kenichi ;
Tomita, Atsuko ;
Tai, Yutaka ;
Shimizu, Ken-ichi .
CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (04) :1064-1069
[4]   Oxidative amide synthesis directly from alcohols with amines [J].
Chen, Cheng ;
Hong, Soon Hyeok .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (01) :20-26
[5]   Nucleosides XI.: Synthesis and antiviral evaluation of 5′-alkylthio-5′-deoxy quinazolinone nucleoside derivatives as S-adenosyl-L-homocysteine analogs [J].
Chien, TC ;
Chen, CS ;
Yu, FH ;
Chern, JW .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (12) :1422-1426
[6]  
Desai P, 1998, ASIAN J CHEM, V10, P615
[7]   Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal Catalysis [J].
Dobereiner, Graham E. ;
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2010, 110 (02) :681-703
[8]   Synthesis of 2-substituted quinazolines via iridium catalysis [J].
Fang, Jie ;
Zhou, Jianguang ;
Fang, Zhijie .
RSC ADVANCES, 2013, 3 (02) :334-336
[9]   Applications of Acceptorless Dehydrogenation and Related Transformations in Chemical Synthesis [J].
Gunanathan, Chidambaram ;
Milstein, David .
SCIENCE, 2013, 341 (6143) :249-+
[10]   CuCl/DABCO/4-HO-TEMPO-Catalyzed Aerobic Oxidative Synthesis of 2-Substituted Quinazolines and 4H-3,1-Benzoxazines [J].
Han, Bing ;
Yang, Xiu-Long ;
Wang, Chao ;
Bai, Yong-Wei ;
Pan, Tai-Chao ;
Chen, Xin ;
Yu, Wei .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) :1136-1142