I2 Promoted Synthesis of 2-Aminothiadiazoles Employing KSCN as a Sulfur Source Under Metal-Free Conditions

被引:11
作者
Zhu, Fuyuan [1 ]
Yan, Zhaohua [1 ]
Ai, Chengmei [1 ]
Wang, Yanmei [1 ]
Lin, Sen [1 ]
机构
[1] Nanchang Univ, Coll Chem, 999 Xuefu Dadao, Nanchang 330031, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
Three-component reaction; Iodine-promoted reaction; Metal-free condition; 2-Aminothiadiazole; Potassium thiocyanate; ONE-POT SYNTHESIS; HURD-MORI-REACTION; 1,3,4-THIADIAZOLE DERIVATIVES; MOLECULAR-IODINE; DEPRESSANT ACTIVITY; MEDIATED SYNTHESIS; N-TOSYLHYDRAZONES; C-N; BOND; 2-AMINO-1,3,4-THIADIAZOLES;
D O I
10.1002/ejoc.201901250
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new three-component strategy from aldehyde, p-toluenesulfonyl hydrazide and potassium thiocyanate for the synthesis of 2-aminothiadiazoles promoted by I-2 under metal-free conditions has been described. Potassium thiocyanate was used as an odorless and low-toxicity sulfur source. A wide range of aromatic aldehydes can smoothly undergo the three-component cyclization reaction under the optimized conditions to give the corresponding products in moderate to good yields.
引用
收藏
页码:6561 / 6565
页数:5
相关论文
共 56 条
[1]   Potential inhibitors of human carbonic anhydrase isozymes I and II: Design, synthesis and docking studies of new 1,3,4-thiadiazole derivatives [J].
Altintop, Mehlika Dilek ;
Sever, Belgin ;
Ozdemir, Ahmet ;
Kucukoglu, Kaan ;
Onem, Hicran ;
Nadaroglu, Hayrunnisa ;
Kaplancikli, Zafer Asim .
BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (13) :3547-3554
[2]   Dithiocarbamate as an efficient intermediate for the synthesis of 2-amino-1,3,4-thiadiazoles in water [J].
Aryanasab, Fezzeh ;
Halimehjani, Azim Ziyaei ;
Saidi, Mohammad R. .
TETRAHEDRON LETTERS, 2010, 51 (05) :790-792
[3]   Photoredox Catalysis of Intramolecular Cyclizations with a Reusable Silica-Bound Ruthenium Complex [J].
Barbante, Gregory J. ;
Ashton, Trent D. ;
Doeven, Egan H. ;
Pfeffer, Frederick M. ;
Wilson, David J. D. ;
Henderson, Luke C. ;
Francis, Paul S. .
CHEMCATCHEM, 2015, 7 (11) :1655-1658
[4]   TBAI-Catalyzed Reaction between N-Tosylhydrazones and Sulfur: A Procedure toward 1,2,3-Thiadiazole [J].
Chen, Jiangfei ;
Jiang, Yan ;
Yu, Jin-Tao ;
Cheng, Jiang .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (01) :271-275
[5]  
Chen K. Z., 2013, ANGEW CHEM, V125, P13566
[6]   Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate [J].
Chen, Xue-Bing ;
Wang, Xue-Quan ;
Song, Jia-Na ;
Yang, Qing-Li ;
Huang, Chao ;
Liu, Wei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (17) :3611-3615
[7]   Copper-Mediated Synthesis of 1,2,3-Triazoles from N-Tosylhydrazones and Anilines [J].
Chen, Zhengkai ;
Yan, Qiangqiang ;
Liu, Zhanxiang ;
Xu, Yiming ;
Zhang, Yuhong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) :13324-13328
[8]   Catalyst and Solvent Free Domino Ring Opening Cyclization: A Greener and Atom Economic Route to 2-Iminothiazolidines [J].
Dahiya, Anjali ;
Ali, Wajid ;
Patel, Bhisma K. .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (03) :4272-4281
[9]   Superior reactivity of thiosemicarbazides in the synthesis of 2-amino-1,3,4-oxadiazoles [J].
Dolman, Sarah J. ;
Gosselin, Francis ;
O'Shea, Paul D. ;
Davies, Ian W. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9548-9551
[10]   One-pot synthesis of 5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one derivatives [J].
Dong, Hong-Ru ;
Gao, Zhong-Lian ;
Li, Rong-Shan ;
Hu, Yi-Ming ;
Dong, Heng-Shan ;
Xie, Zhi-Xiang .
RSC ADVANCES, 2014, 4 (99) :55827-55831