Expedient synthesis of tetrahydroquinoline-3-spirohydantoin derivatives via the Lewis acid-catalyzed tert-amino effect reaction

被引:26
作者
Briones, John F. [1 ,2 ]
Basarab, Gregory S. [1 ,3 ]
机构
[1] AstraZeneca R&D Boston, Infect Innovat Med, 35 Gatehouse Dr, Waltham, MA 02451 USA
[2] Moderna Therapeut, 200 Technol Sq, Cambridge, MA 02139 USA
[3] Univ Cape Town, Dept Chem, Drug Discovery & Dev Ctr, ZA-7700 Rondebosch, South Africa
关键词
C-H FUNCTIONALIZATION; SPIROOXINDOLE TETRAHYDROQUINOLINES; 1,5-HYDRIDE TRANSFER/CYCLIZATION; SPIROHYDANTOINS; CLOSURE; AGENT;
D O I
10.1039/c6cc03600g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Magnesium triflate was found to effectively catalyze the tert-amino effect reaction (T-reaction) involving ethyl 3-(2-(dialkylamino)phenyl)-2-nitroacrylates leading to tetrahydroquinoline nitroester derivatives. These compounds can be readily transformed to the corresponding valuable spirohydantoin derivatives.
引用
收藏
页码:8541 / 8544
页数:4
相关论文
共 34 条
[1]   Stereoselective Synthesis of Indoline, Tetrahydroquinoline, and Tetrahydrobenzazepine Derivatives from o-Bromophenyl N-tert-Butylsulfinyl Aldimines [J].
Alberto Sirvent, Juan ;
Foubelo, Francisco ;
Yus, Miguel .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03) :1356-1367
[2]  
Barbachyn M. R, 2004, WO Patent, Patent No. [2004031195, W02004031195 Al]
[3]  
Barbachyn M.R, 2007, U.S. Patent, Patent No. [7,208,490 B2, 7208490]
[4]   Magnesium perchlorate as efficient Lewis acid for the Knoevenagel condensation between β-diketones and aldehydes [J].
Bartoli, Giuseppe ;
Bosco, Marcella ;
Carlone, Armando ;
Dalpozzo, Renato ;
Galzerano, Patrizia ;
Melchiorre, Paolo ;
Sambri, Letizia .
TETRAHEDRON LETTERS, 2008, 49 (16) :2555-2557
[5]   Responding to the challenge of untreatable gonorrhea: ETX0914, a first-in-class agent with a distinct mechanism-of-action against bacterial Type II topoisomerases [J].
Basarab, Gregory S. ;
Kern, Gunther H. ;
McNulty, John ;
Mueller, John P. ;
Lawrence, Kenneth ;
Vishwanathan, Karthick ;
Alm, Richard A. ;
Barvian, Kevin ;
Doig, Peter ;
Galullo, Vincent ;
Gardner, Humphrey ;
Gowravaram, Madhusudhan ;
Huband, Michael ;
Kimzey, Amy ;
Morningstar, Marshall ;
Kutschke, Amy ;
Lahiri, Sushmita D. ;
Perros, Manos ;
Singh, Renu ;
Schuck, Virna J. A. ;
Tommasi, Ruben ;
Walkup, Grant ;
Newman, Joseph V. .
SCIENTIFIC REPORTS, 2015, 5
[6]   Synthesis of a Tetrahydronaphthyridine Spiropyrimidinetrione DNA Gyrase Inhibiting Antibacterial Agent - Differential Substitution at all Five Carbon Atoms of Pyridine. [J].
Basarab, Gregory S. ;
Galullo, Vincent ;
DeGrace, Nancy ;
Hauck, Sheila ;
Joubran, Camil ;
Wesolowski, Steven S. .
ORGANIC LETTERS, 2014, 16 (24) :6456-6459
[7]   Novel DNA Gyrase Inhibiting Spiropyrimidinetriones with a Benzisoxazole Scaffold: SAR and in Vivo Characterization [J].
Basarab, Gregory S. ;
Brassil, Patrick ;
Doig, Peter ;
Galullo, Vincent ;
Haimes, Howard B. ;
Kern, Gunther ;
Kutschke, Amy ;
McNulty, John ;
Schuck, Virna J. A. ;
Stone, Gregory ;
Gowravaram, Madhusudhan .
JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (21) :9078-9095
[8]   Asymmetric Tandem 1,5-Hydride Shift/Ring Closure for the Synthesis of Chiral Spirooxindole Tetrahydroquinolines [J].
Cao, Weidi ;
Liu, Xiaohua ;
Guo, Jing ;
Lin, Lili ;
Feng, Xiaoming .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (04) :1632-1636
[9]   Highly Enantioselective Synthesis of Tetrahydroquinolines via Cobalt(II)-Catalyzed Tandem 1,5-Hydride Transfer/Cyclization [J].
Cao, Weidi ;
Liu, Xiaohua ;
Wang, Wentao ;
Lin, Lili ;
Feng, Xiaoming .
ORGANIC LETTERS, 2011, 13 (04) :600-603
[10]   Catalytic Enantioselective tert-Aminocyclization by Asymmetric Binary Acid Catalysis (ABC): Stereospecific 1,5-Hydrogen Transfer [J].
Chen, Liujuan ;
Zhang, Long ;
Lv, Jian ;
Cheng, Jin-Pei ;
Luo, Sanzhong .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (29) :8891-8895