Interaction of 4-Oxo-4H-pyrazolo[5,1-c][1,2,4]triazin-1-ides with Grignard Reagents

被引:10
作者
Ivanov, Sergey M. [1 ]
Shestopalov, Anatoliy M. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Prospekt 47, Moscow 119991, Russia
关键词
DERIVATIVES; REACTIVITY; PYRAZOLO; SYSTEM;
D O I
10.1002/jhet.3236
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reactions of magnesium 3-tert-butyl-8-R-4-oxo-4H-pyrazolo[5,1-c][1,2,4]triazin-1-ides (R=CN, CO2Et) with AlkMgBr led to nucleophilic additions to either side chain or triazine core, with selectivity being dependent on the nature of substituents, as well as on the solvents used. Previously inaccessible C-8-functionalized and C-4-functionalized pyrazolo[5,1-c][1,2,4]triazines and 3-tert-butyl-3-ethyl-4-oxo-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine were synthesized, and their reactivity and spectral data discussed.
引用
收藏
页码:1966 / 1972
页数:7
相关论文
共 29 条
[1]   Synthesis, antibacterial activity and cytotoxicity of new fused pyrazolo [1,5-a]pyrimidine and pyrazolo[5,1-c][1,2,4]triazine derivatives from new 5-aminopyrazoles [J].
Al-Adiwish, Wedad M. ;
Tahir, M. I. M. ;
Siti-Noor-Adnalizawati, A. ;
Hashim, Siti Farah ;
Ibrahim, Nazlina ;
Yaacob, W. A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 64 :464-476
[2]   Stereoselective synthesis of dihydrothiadiazinoazines and dihydrothiadiazinoazoles and their pyrolytic desulfurization ring contraction [J].
Al-Etaibi, Alya ;
John, Elizabeth ;
Ibrahim, Maher R. ;
Al-Awadi, Nouria A. ;
Ibrahim, Yehia A. .
TETRAHEDRON, 2011, 67 (34) :6259-6274
[3]  
Allen CFH, 1926, ORG SYNTH, V6, P32
[4]  
[Anonymous], RUSS J ORG CHEM
[5]  
[Anonymous], 884140 CCDC
[6]  
[Anonymous], J HETEROCYCLIC CHEM
[7]   Synthesis, reactions, and antiviral activity of 1-(1H-pyrazolo[3,4-b]pyridin-5-yl)ethanone and pyrido[2′,3′: 3,4]pyrazolo[5,1-c][1,2,4]triazine derivatives [J].
Attaby, Fawzy A. ;
Elghandour, A. H. H. ;
Ali, M. A. ;
Ibrahem, Yasser M. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (05) :1087-1102
[8]  
Charushin V. N., 2008, COMPREHENSIVE HETERO, V9, P95, DOI DOI 10.1016/B978-008044992-0.00802-6
[9]  
Dalinger IL, 2010, RUSS CHEM B+, V59, P1631, DOI 10.1007/s11172-010-0287-9
[10]   Pyridazine derivatives and related compounds.: Part 13:: Synthesis and antimicrobial activity of some pyridazino[3′,4′:3,4]pyrazolo[5,1-c]-1,2,4-triazines [J].
Deeb, A ;
El-Mariah, F ;
Hosny, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (19) :5013-5017