An efficient and facile synthesis of new tetracyclic fused pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones

被引:4
作者
Gomaa, Mohsen A. -M. [1 ]
Ali, Huda A. [1 ]
机构
[1] Menia Univ, Dept Chem, Fac Sci, El Minia 61519, Egypt
关键词
Pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolone; Amidrazone; (1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile; Dearomatization; NITROGEN SYSTEMS BEARING; POTENTIAL ANTI-HIV; ENANTIOSELECTIVE CONSTRUCTION; 1,3-DIPOLAR CYCLOADDITIONS; 1,2,4-TRIAZINE MOIETY; ANTICANCER DRUGS; AMIDRAZONES; FLUORINE;
D O I
10.1007/s11030-018-9849-9
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Reaction of amidrazones 1a-1i with (1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile (2) in ethyl acetate solution in one-step reaction led to the formation of unprecedented pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones 3a-3g along with pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-12b-oles 3h-3m in moderate to excellent yields. These novel heterocycles were formed via a Michael addition reaction followed by intramolecular cyclization via a dearomatization process.
引用
收藏
页码:969 / 977
页数:9
相关论文
共 35 条
[31]   Enantioselective Construction of Spiro[indoline-3,2′-pyrrole] Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions Using Allenes as Equivalents of Alkynes [J].
Wang, Cong-Shuai ;
Zhu, Ren-Yi ;
Zheng, Jian ;
Shi, Feng ;
Tu, Shu-Jiang .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01) :512-520
[32]   Catalytic asymmetric chemoselective 1,3-dipolar cycloadditions of an azomethine ylide with isatin-derived imines: diastereo- and enantioselective construction of a spiro[imidazolidine-2,3′-oxindole] framework [J].
Wang, Yue-Ming ;
Zhang, Hong-Hao ;
Li, Can ;
Fan, Tao ;
Shi, Feng .
CHEMICAL COMMUNICATIONS, 2016, 52 (09) :1804-1807
[33]   Discovery of a 2,4-Disubstituted Pyrrolo[1,2-f][1,2,4]triazine Inhibitor (BMS-754807) of Insulin-like Growth Factor Receptor (IGF-1R) Kinase in Clinical Development [J].
Wittman, Mark D. ;
Carboni, Joan M. ;
Yang, Zheng ;
Lee, Francis Y. ;
Antman, Melissa ;
Attar, Ricardo ;
Balimane, Praveen ;
Chang, Chiehying ;
Chen, Cliff ;
Discenza, Lorell ;
Frennesson, David ;
Gottardis, Marco M. ;
Greer, Ann ;
Hurlburt, Warren ;
Johnson, Walter ;
Langley, David R. ;
Li, Aixin ;
Li, Jianqing ;
Liu, Peiying ;
Mastalerz, Harold ;
Mathur, Arvind ;
Menard, Krista ;
Patel, Karishma ;
Sack, John ;
Sang, Xiaopeng ;
Saulnier, Mark ;
Smith, Daniel ;
Stefanski, Kevin ;
Trainor, George ;
Velaparthi, Upender ;
Zhang, Guifen ;
Zimmermann, Kurt ;
Vyas, Dolatrai M. .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (23) :7360-7363
[34]   Organocatalytic Asymmetric Arylative Dearomatization of 2,3-Disubstituted Indoles Enabled by Tandem Reactions [J].
Zhang, Yu-Chen ;
Zhao, Jia-Jia ;
Jiang, Fei ;
Sun, Si-Bing ;
Shi, Feng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (50) :13912-13915
[35]   Broadening the scope of 1,2,4-triazine synthesis by the application of microwave technology [J].
Zhao, ZJ ;
Leister, WH ;
Strauss, KA ;
Wisnoski, DD ;
Lindsley, CW .
TETRAHEDRON LETTERS, 2003, 44 (06) :1123-1127