A green approach for synthesis of naphthoquinone-fused oxazine derivatives in water under ultrasonic irradiation

被引:6
作者
Cao, Ya-Qian [1 ]
Li, Xin-Ran [1 ]
Wu, Wei [1 ]
Zhang, Dan [1 ]
Zhang, Zhan-Hui [1 ]
Mo, Li-Ping [1 ]
机构
[1] Hebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050024, Peoples R China
基金
中国国家自然科学基金;
关键词
1,4-Naphthoquinone; 1,3-Oxazine; Ultrasound; Water; Multicomponent reaction; POT 3-COMPONENT SYNTHESIS; MULTICOMPONENT REACTIONS; COMBINATORIAL SYNTHESIS; SUBSTITUTED PYRROLES; EFFICIENT CATALYST; MEGLUMINE; INHIBITORS; CHEMISTRY; SOLVENTS; BEARING;
D O I
10.1007/s11164-016-2854-7
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient and eco-friendly procedure has been developed for synthesis of naphthoquinone-fused oxazine derivatives via one-pot pseudo four-component reaction of 2-hydroxy-1,4-naphthoquinone, aromatic amine and formaldehyde in water under ultrasound irradiation. This protocol has the advantages of being catalyst-free, with short reaction times and high yields, and being environmentally benign with an easy work-up.
引用
收藏
页码:3745 / 3755
页数:11
相关论文
共 44 条
[1]   Recent developments on ultrasound assisted catalyst-free organic synthesis [J].
Banerjee, Bubun .
ULTRASONICS SONOCHEMISTRY, 2017, 35 :1-14
[2]   Recent developments on ultrasound-assisted one-pot multicomponent synthesis of biologically relevant heterocycles [J].
Banerjee, Bubun .
ULTRASONICS SONOCHEMISTRY, 2017, 35 :15-35
[3]   Modified Salicylanilide and 3-Phenyl-2H-benzo[e][1,3]oxazine-2,4(3H)-dione Derivatives as Novel Inhibitors of Osteoclast Differentiation and Bone Resorption [J].
Chen, Chun-Liang ;
Liu, Fei-Lan ;
Lee, Chia-Chung ;
Chen, Tsung-Chih ;
Ali, Ahmed Atef Ahmed ;
Sytwu, Huey-Kang ;
Chang, Deh-Ming ;
Huang, Hsu-Shan .
JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (19) :8072-8085
[4]   Solvent-Free and Catalysts-Free Chemistry: A Benign Pathway to Sustainability [J].
Gawande, Manoj B. ;
Bonifacio, Vasco D. B. ;
Luque, Rafael ;
Branco, Paula S. ;
Varma, Rajender S. .
CHEMSUSCHEM, 2014, 7 (01) :24-44
[5]   Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis [J].
Gawande, Manoj B. ;
Bonifacio, Vasco D. B. ;
Luque, Rafael ;
Branco, Paula S. ;
Varma, Rajender S. .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) :5522-5551
[6]   Multicomponent reactions in unconventional solvents: state of the art [J].
Gu, Yanlong .
GREEN CHEMISTRY, 2012, 14 (08) :2091-2128
[7]   Meglumine: A Novel and Efficient Catalyst for One-Pot, Three-Component Combinatorial Synthesis of Functionalized 2-Amino-4H-pyrans [J].
Guo, Rui-Yun ;
An, Zhi-Min ;
Mo, Li-Ping ;
Wang, Rui-Zhi ;
Liu, Hong-Xia ;
Wang, Shu-Xia ;
Zhang, Zhan-Hui .
ACS COMBINATORIAL SCIENCE, 2013, 15 (11) :557-563
[8]   One-pot three-component synthesis of functionalized spirooxindoles in gluconic acid aqueous solution [J].
Guo, Rui-Yun ;
Wang, Ping ;
Wang, Guo-Dong ;
Mo, Li-Ping ;
Zhang, Zhan-Hui .
TETRAHEDRON, 2013, 69 (08) :2056-2061
[9]   Reaction solvent selection: The potential of water as a solvent for organic transformations [J].
Hailes, Helen C. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) :114-120
[10]   Deep eutectic solvent based on choline chloride and malonic acid as an efficient and reusable catalytic system for one-pot synthesis of functionalized pyrroles [J].
Hu, Hai-Chuan ;
Liu, Yu-Heng ;
Li, Bao-Le ;
Cui, Zhen-Shui ;
Zhang, Zhan-Hui .
RSC ADVANCES, 2015, 5 (10) :7720-7728