Synthesis of New [1,2,4]Triazolo[1,5-a]pyrimidine Derivatives: Reactivity of 3-Amino[1,2,4]triazole towards Enaminonitriles and Enaminones

被引:13
作者
Alnajjar, Abdulaziz [1 ]
Abdelkhalik, Mervat Mohammed [1 ]
Raslan, Mohamed Abdelmonem [2 ]
Ibraheem, Solwan Maher [2 ]
Sadek, Kamal Usef [3 ]
机构
[1] Publ Author Appl Educ & Training, Appl Sci Dept, Coll Technol Studies, POB 42325, Safat 70654, Kuwait
[2] Aswan Univ, Chem Dept, Fac Sci, Aswan 81528, Egypt
[3] Menia Univ, Chem Dept, Fac Sci, Al Minya 61519, Egypt
关键词
AGENTS;
D O I
10.1002/jhet.3222
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A diversity of new 7-substituted[1,2,4]triazolo[1,5-a]pyrimidine and 6-substituted[1,2,4]triazolo[1,5-a]pyrimidine-7-amine derivatives has been synthesized via reaction of 3-amino-[1,2,4]triazole with enaminonitriles and enaminones. The regio orientation and the structure of the products were confirmed by spectral and analytical data and synthesis via an alternative route. The procedure proved to be simple, efficient, and high yielding, and diversities of [1,2,4]triazolo[1,5-a]pyrimidines were obtained.
引用
收藏
页码:1804 / 1808
页数:5
相关论文
共 26 条
[1]   Microwave-assisted reactions:: Part 2 -: One-pot synthesis of pyrimido[1,2-a]pyrimidines [J].
Abd El Latif, RM ;
Barsy, MA ;
Aref, AM ;
Sadek, KU .
GREEN CHEMISTRY, 2002, 4 (03) :196-198
[2]   Fluorinated 1,2,4-Triazolo[1,5-a]pyrimidine-6-carboxylic Acid Derivatives as Antimycobacterial Agents [J].
Abdel-Rahman, Hamdy M. ;
El-Koussi, Nawal A. ;
Hassan, Hoda Y. .
ARCHIV DER PHARMAZIE, 2009, 342 (02) :94-99
[3]   Cu-Catalyzed Aerobic Oxidative Cyclization of Guanidylpyridines and Derivatives [J].
Bartels, Bjoern ;
Bolas, Conor Gordon ;
Cueni, Philipp ;
Fantasia, Serena ;
Gaeng, Nicolas ;
Trita, Andrada Stefania .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02) :1249-1257
[4]   Pyrazole clubbed triazolo[1,5-a]pyrimidine hybrids as an anti-tubercular agents: Synthesis, in vitro screening and molecular docking study [J].
Bhatt, Jaimin D. ;
Chudasama, Chaitanya J. ;
Patel, Kanuprasad D. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (24) :7711-7716
[5]   Cyclocondensation of N-aryl-3-oxobutanethioamides with 1H-1,2,4-triazol-5-amine [J].
Britsun, V. N. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (10) :1528-1531
[6]   Synthesis, antifungal activity and CoMFA analysis of novel l,2,4-triazolo[1,5-a]pyrimidine derivatives [J].
Chen, Qiong ;
Zhu, Xiao-Lei ;
Jiang, Li-Li ;
Liu, Zu-Ming ;
Yang, Guang-Fu .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (03) :595-603
[7]   Essramycin: A first triazolopyrimidine antibiotic isolated from nature [J].
El-Gendy, Mervat M. A. ;
Shaaban, Mohamed ;
Shaaban, Khaled A. ;
El-Bondkly, Ahmed M. ;
Laatsch, Hartmut .
JOURNAL OF ANTIBIOTICS, 2008, 61 (03) :149-157
[8]   Ultrasound irradiation promotes the synthesis of new 1,2,4-triazolo [1,5-a]pyrimidine [J].
Frizzo, Clarissa P. ;
Scapin, Elisandra ;
Marzari, Mara R. B. ;
Muenchen, Taiana S. ;
Zanatta, Nilo ;
Bonacorso, Helio G. ;
Buriol, Lilian ;
Martins, Marcos A. P. .
ULTRASONICS SONOCHEMISTRY, 2014, 21 (03) :958-962
[9]   Base-catalyzed one-step synthesis of 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidines [J].
He, Xinhua ;
Kassab, Shaymaa E. ;
Heinzl, Geoffrey ;
Xue, Fengtian .
TETRAHEDRON LETTERS, 2015, 56 (08) :1034-1037
[10]   Evidence for a Common Pharmacological Interaction Site on KCa2 Channels Providing Both Selective Activation and Selective Inhibition of the Human KCa2.1 Subtype [J].
Hougaard, Charlotte ;
Hammami, Sofia ;
Eriksen, Birgitte L. ;
Sorensen, Ulrik S. ;
Jensen, Marianne L. ;
Strobaek, Dorte ;
Christophersen, Palle .
MOLECULAR PHARMACOLOGY, 2012, 81 (02) :210-219