Synthesis of 5-(4-bromophenyl)- and 5-(5-bromothiophen-2-yl)-substituted 3-aryl[1,2,4]triazolo[4,3-c]quinazolines

被引:6
作者
Nosova, E., V [1 ,2 ]
Kopotilova, A. E. [1 ]
Ivan'kina, M. A. [1 ]
Moshkina, T. N. [1 ]
Kopchuk, D. S. [1 ,2 ]
机构
[1] Ural Fed Univ, 19 Ul Mira, Ekaterinburg 620002, Russia
[2] Russian Acad Sci, I Ya Postovskii Inst Organ Synth, Ural Branch, 20 Ul S Kovalevskoi, Ekaterinburg 620219, Russia
关键词
1; 2; 4]triazolo[4; 3-c]quinazolines; oxidative cyclization; 2-(4-bromophenyl)quinazolin-4-one; 4-hydrazinoquinazolines; hydrazones; SAR;
D O I
10.1007/s11172-022-3554-7
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of [1,2,4]triazolo[4,3-c]quinazolines, bearing 3-positioned p-bromophenyl or 5-bromothiophen-2-yl fragment, was synthesized by oxidative cyclization of the corresponding hydrazones with bromine in glacial acetic acid at room temperature. The obtained tricyclic derivatives are valuable intermediates for biologically active compounds and fluorophores.
引用
收藏
页码:1483 / 1487
页数:5
相关论文
共 50 条
[31]   Synthesis of 5-[(acetylhydrazono)-(4-chlorophenyl)-methyl]thiophen-2-yl ester of the trifluoromethanesulfonic acid [J].
Pascual, A .
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1999, 341 (07) :695-700
[32]   The 3-(4-(Benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine [J].
Doherty, Katrina E. ;
Sandoval, Arturo Leon ;
Mercier, Ethan T. ;
Leadbeater, Nicholas E. .
MOLBANK, 2023, 2023 (03)
[33]   Synthesis of 8-Bromo-7-chloro[1,2,4]triazolo[4,3-c]pyrimidines, Their Ring Rearrangement to [1,5-c] Analogues, and Further Diversification [J].
Tang, Caifei ;
Wang, Chao ;
Li, Zhiming ;
Wang, Quanrui .
SYNTHESIS-STUTTGART, 2014, 46 (20) :2734-2746
[34]   A facile and practical one-pot synthesis of [1,2,4]-triazolo[4,3-a]pyridines [J].
Vadagaonkar, Kamlesh S. ;
Murugan, Kaliyappan ;
Chaskar, Atul C. ;
Bhate, Prakash M. .
RSC ADVANCES, 2014, 4 (64) :34056-34064
[35]   A novel mild method for the synthesis of 3-amino-4-(5-aryl-1H-1,2,4-triazol-3-yl)furazans [J].
Semyakin, Svyatoslav S. ;
Struchkova, Marina I. ;
Sheremetev, Aleksei B. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (05) :346-349
[36]   A Novel Mild Method for the Synthesis of 3-Amino-4-(5-aryl-1H-1,2,4-Triazol-3-yl)Furazans [J].
Svyatoslav S. Semyakin ;
Marina I. Struchkova ;
Aleksei B. Sheremetev .
Chemistry of Heterocyclic Compounds, 2016, 52 :346-349
[37]   Copper(II) chloride mediated synthesis and DNA photocleavage activity of 1-aryl/heteroaryl-4-substituted-1,2,4-triazolo[4,3-a]quinoxalines [J].
Aggarwal, Ranjana ;
Sumran, Garima ;
Kumar, Virender ;
Mittal, Ashwani .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (12) :6083-6088
[38]   Synthesis of 1, 4-Bis[3-N-propionyl-2-aryl-1, 3, 4- oxadiazoline-5-yl]phenylenes [J].
De Jiang LI He Qing FU Department of Chemistry Yunyang Teachers College Hubei Institute of Chemical Engineering South China University of Technology Guangzhou .
Chinese Chemical Letters, 2006, (05) :625-627
[39]   Synthesis and tautomerism of 2-[3(5)-aryl(methyl)pyrazol-4-yl]-1- benzimidazoles [J].
Dzvinchuk I.B. ;
Lozinskii M.O. .
Chemistry of Heterocyclic Compounds, 2006, 42 (9) :1190-1196
[40]   Ethyl 4-(1,2,3-Thiadiazol-4-yl)-5-(bromomethyl)furan-2-carboxylate and Its Reactions with Nucleophiles [J].
Remizov, Yu O. ;
Pevzner, L. M. ;
Petrov, M. L. ;
Ponyaev, A. I. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2015, 85 (12) :2728-2734