Hexahydrospiro-pyrazolo[3,4-b]pyridine-4,1-pyrrolo[3,2,1-ij]quinolines Derived from 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

被引:10
作者
Saatluo, Bahman Ebrahimi [1 ]
Baradarani, Mehdi M. [1 ]
Joule, John A. [2 ]
机构
[1] Univ Urmia, Fac Chem, Orumiyeh 57153165, Iran
[2] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
关键词
SPIROOXINDOLE NATURAL-PRODUCTS; AZOMETHINE YLIDES; ONE-POT; DERIVATIVES; INHIBITORS; ISATIN;
D O I
10.1002/jhet.3150
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The tricyclic isatin, 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione (1), reacts with a combination of an aryl cyanomethyl ketone 8 and a 5-amino-1-arylpyrazole 7 to generate spirocyclic products 9.
引用
收藏
页码:1176 / 1182
页数:7
相关论文
共 30 条
[1]   Spiro[4H-pyran-3,3-oxindoles] Derived from 9,10-dihydroacridine [J].
Alipour, Mousa ;
Baradarani, Mehdi M. ;
Joule, John A. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (04) :2223-2227
[2]   Spiro[4H-pyran-3,3-oxindoles] Derived from 1,2,3,4-tetrahydroquinolinePart 2 [J].
Baradarani, Mehdi M. ;
Khoshsirat, Sahar ;
Moharampour, Mehri ;
Ebrahimisaatlo, Bahman ;
Rashidi, Ahmad ;
Rozycka-Sokolowska, Ewa ;
Joule, John A. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (02) :944-951
[3]   Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G [J].
Baran, PS ;
Richter, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15394-15396
[4]   Synthesis of novel spirooxindole derivatives by one pot multicomponent reaction and their antimicrobial activity [J].
Bhaskar, Gangaru ;
Arun, Yuvaraj ;
Balachandran, Chandrasekar ;
Saikumar, Chandrasekara ;
Perumal, Paramasivan T. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 51 :79-91
[5]   Enantiomers of an Indole Alkaloid Containing Unusual Dihydrothiopyran and 1,2,4-Thiadiazole Rings from the Root of Isatis indigotica [J].
Chen, Minghua ;
Lin, Sheng ;
Li, Li ;
Zhu, Chenggen ;
Wang, Xiaoliang ;
Wang, Yanan ;
Jiang, Bingya ;
Wang, Sujuan ;
Li, Yuhuan ;
Jiang, Jiandong ;
Shi, Jiangong .
ORGANIC LETTERS, 2012, 14 (22) :5668-5671
[6]   Tetracyclic spirooxindole blockers of hNaV1.7: activity in vitro and in CFA-induced inflammatory pain model [J].
Chowdhury, Sultan ;
Liu, Shifeng ;
Cadieux, Jay A. ;
Hsieh, Tom ;
Chafeev, Mikhail ;
Sun, Shaoyi ;
Jia, Qi ;
Sun, Jianyu ;
Wood, Mark ;
Langille, Jonathan ;
Sviridov, Serguei ;
Fu, Jianmin ;
Zhang, Zaihui ;
Chui, Ray ;
Wang, Audrey ;
Cheng, Xing ;
Zhong, Jing ;
Hossain, Sazzad ;
Khakh, Kuldip ;
Rajlic, Ivana ;
Verschoof, Henry ;
Kwan, Rainbow ;
Young, Wendy .
MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (04) :1825-1836
[7]   Pd-Catalyzed Assembly of Spirooxindole Natural Products: A Short Synthesis of Horsfiline [J].
Deppermann, Nina ;
Thomanek, Heike ;
Prenzel, Alexander H. G. P. ;
Maison, Wolfgang .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (17) :5994-6000
[8]   Direct N-H/α,α,β,β-C(sp3)-H functionalization of piperidine via an azomethine ylide route: synthesis of spirooxindoles bearing 3-substituted oxindoles [J].
Du, Yanlong ;
Yu, Aimin ;
Jia, Jiru ;
Zhang, Youquan ;
Meng, Xiangtai .
CHEMICAL COMMUNICATIONS, 2017, 53 (10) :1684-1687
[9]   Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3+2]-Cycloaddition [J].
Filatov, Alexander S. ;
Knyazev, Nickolay A. ;
Molchanov, Alexander P. ;
Panikorovsky, Taras L. ;
Kostikov, Rafael R. ;
Larina, Anna G. ;
Boitsov, Vitali M. ;
Stepakov, Alexander V. .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (02) :959-975
[10]   Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents [J].
Galliford, Chris V. ;
Scheidt, Karl A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8748-8758