Photo-promoted cascade cyclization of aryl alkynes: access to thiocyanate/trifluoromethylthio-containing quinolino[2,1-b]quinazolinones

被引：7
作者：
Fan, Jie [1 ]
Yan, Qinqin [1 ]
Liu, Huaqing [1 ]
Li, Lijun [1 ]
Liu, Zhong-Quan [2 ]
Li, Zejiang [1 ]
机构：
[1] Hebei Univ, Coll Chem & Mat Sci, Key Lab Med Chem & Mol Diag, Key Lab Chem Biol Hebei Prov,Minist Educ,State Key, Baoding 071002, Hebei, Peoples R China
[2] Nanjing Univ Chinese Med, Coll Pharm, Jiangsu Collaborat Innovat Ctr Chinese Med Resourc, Nanjing 210023, Jiangsu, Peoples R China
来源：
NEW JOURNAL OF CHEMISTRY | 2023年 / 47卷 / 45期
基金：
中国国家自然科学基金;
关键词：
ALPHA-THIOCYANATION; C-3; THIOCYANATION; QUINAZOLINONES; DERIVATIVES; HALIDES; ROUTE; TRIFLUOROMETHYLTHIOLATION; EFFICIENT;
D O I：
10.1039/d3nj04433e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Photo-promoted cascade cyclization of aryl alkynes with NH4SCN has been reported for the construction of diverse SCN-containing quinolino[2,1-b]quinazolinones. SCF3-containing fused cyclic compounds could also be obtained with high yields. In addition, a variety of scaled-up reactions, transformation operations, radical inhibition experiments, and on/off light studies were undertaken to support the merits and reaction mechanism of this tandem system. Finally, we confirmed the skeleton of the desired product via single-crystal X-ray diffraction.
引用
收藏
页码：20713 / 20717
页数：5
相关论文
共 63 条
[1]   I2-Promoted [3+2] Cyclization of 1,3-Diketones with Potassium Thiocyanate: a Route to Thiazol-2(3H)-One Derivatives [J].
An, Zhenyu ;
Liu, Yafeng ;
Zhao, Pengbo ;
Yan, Rulong .
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (13) :3240-3244
[2]   Regiodivergent C-N Coupling of Quinazolinones Controlled by theDipole Moments of Tautomers [J].
Bera, Shyamal Kanti ;
Mal, Prasenjit .
ORGANIC LETTERS, 2022, 24 (17) :3144-3148
[3]   Copper-Catalyzed Thiolation of Terminal Alkynes Employing Thiocyanate as the Sulfur Source Leading to Enaminone-Based Alkynyl Sulfides under Ambient Conditions [J].
Chandran, R. ;
Pise, Ashwini ;
Shah, Suraj Kumar ;
Rahul, D. ;
Suman, V ;
Tiwari, Keshri Nath .
ORGANIC LETTERS, 2020, 22 (16) :6557-6561
[4]   Electrophotocatalytic tri- or difluoromethylative cyclization of alkenes [J].
Chen, Danna ;
Yang, Xuege ;
Wang, Dongyin ;
Li, Yanni ;
Shi, Lou ;
Liang, Deqiang .
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (10) :2482-2490
[5]   Recent progress of direct thiocyanation reactions [J].
Chen, Haixin ;
Shi, Xiaotian ;
Liu, Xiang ;
Zhao, Limin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (33) :6508-6527
[6]   A facile approach for the trifluoromethylthiolation of methylenecyclopropanes [J].
Chen, Min-Tao ;
Tang, Xiang-Ying ;
Shi, Min .
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (01) :86-90
[7]   Photo-induced spirocyclization of biaryl ynones with ammonium thiocyanate: access to thiocyanate-featured spiro[5,5]trienones [J].
Chen, Shiliu ;
Yan, Qinqin ;
Fan, Jie ;
Guo, Changyou ;
Li, Lijun ;
Liu, Zhong-Quan ;
Li, Zejiang .
GREEN CHEMISTRY, 2023, 25 (01) :153-160
[8]   Photoinduced cascade cyclization of alkynes with NH4SCN: access to SCN-containing dibenzazepines or dioxodibenzothiazepines [J].
Chen, Shiliu ;
Yan, Qinqin ;
Fan, Jie ;
Gao, Yongjun ;
Yang, Xiulong ;
Li, Lijun ;
Liu, Zhongquan ;
Li, Zejiang .
GREEN CHEMISTRY, 2022, 24 (12) :4742-4747
[9]   Visible-Light-Induced Radical Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Quinazolinones [J].
Chen, Xiaoyu ;
Liu, Bo ;
Pei, Congcong ;
Li, Jingya ;
Zou, Dapeng ;
Wu, Yangjie ;
Wu, Yusheng .
ORGANIC LETTERS, 2021, 23 (20) :7787-7791
[10]   Palladium-Catalyzed Site-Selective sp3 C-H Bond Thiocyanation of 2-Aminofurans [J].
Chen, Yongtao ;
Wang, Shuaifeng ;
Jiang, Qianwen ;
Cheng, Cungui ;
Xiao, Xiaohui ;
Zhu, Gangguo .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (02) :716-722
1234567