Synthesis and structure of functionalized podands containing 4,7-dihydrotetrazolo[1,5-a]pyrimidine ring. Differently substituted dihydropyrimidine podands

被引:4
作者
Filatova, Elena S. [1 ,2 ]
Fedorova, Olga V. [1 ]
Slepukhin, Pavel A. [1 ,2 ]
Rusinov, Gennady L. [1 ,2 ]
Charushin, Valery N. [1 ,2 ]
机构
[1] Russian Acad Sci, Ural Branch, I Ya Postovsky Inst Organ Synth, 22 S Kovalevskoi,20 Akad Skaya St, Ekaterinburg 620990, Russia
[2] Ural Fed Univ, 19 Mira St, Ekaterinburg 620002, Russia
基金
俄罗斯科学基金会;
关键词
dihydropyrimidine thione podands; 4,7-dihydrotetrazolo[1,5-a]pyrimidine podands; differently substituted podands; transport polyether spacer; Biginelli reaction;
D O I
10.1007/s10593-018-2373-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 3-oxobutanoate-containing polyethers with benzaldehyde and 5-aminotetrazole in the presence of polyphosphoric acid was used to synthesize podands containing two terminal tetrazolo[1,5-a] dihydropyrimidine groups. Byproducts were isolated and identified as podands containing different substituents - one 4,7-dihydrotetrazolo[1,5-a] pyrimidine ring system and a free hydroxy group at the other terminus of the polyether chain. Analogous differently substituted podands, including one 3,4-dihydropyrimidine-2(1H)-thione moiety, were isolated from the reactions of 3-oxobutanoate-containing polyethers with benzaldehyde and thiourea.
引用
收藏
页码:971 / 976
页数:6
相关论文
共 31 条
[1]  
Contreras JM, 2008, PRACTICE OF MEDICINAL CHEMISTRY, 3RD EDITION, P380, DOI 10.1016/B978-0-12-374194-3.00018-4
[2]  
Cuconati A., US Patent, Patent No. 2009088397
[3]   Synthesis and activity of novel homodimers of Morita-Baylis-Hillman adducts against Leishmania donovani: A twin drug approach [J].
da Silva, Wagner A. V. ;
Rodrigues, Daniele C. ;
de Oliveira, Ramon G. ;
Mendes, Rhuan K. S. ;
Olegario, Tayna R. ;
Rocha, Juliana C. ;
Keesen, Tatjana S. L. ;
Lima-Junior, Claudio G. ;
Vasconcellos, Mario L. A. A. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (18) :4523-4526
[4]  
Danagulyan G. G., 2017, CHEM J ARM, V70, P113
[5]   OLEX2: a complete structure solution, refinement and analysis program [J].
Dolomanov, Oleg V. ;
Bourhis, Luc J. ;
Gildea, Richard J. ;
Howard, Judith A. K. ;
Puschmann, Horst .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341
[6]   5-AMINOTETRAZOLE AS A BUILDING BLOCK FOR MULTICOMPONENT REACTIONS [J].
Dolzhenko, Anton V. .
HETEROCYCLES, 2017, 94 (10) :1819-1846
[7]   Multicomponent reactions in the synthesis of dihydropyrimidine-containing podands having tuberculostatic activity [J].
Fedorova, O. V. ;
Filatova, E. S. ;
Titova, Yu. A. ;
Kravchenko, M. A. ;
Medvinskiy, I. D. ;
Rusinov, G. L. ;
Charushin, V. N. .
RUSSIAN CHEMICAL BULLETIN, 2018, 67 (04) :743-746
[8]   Synthesis and Tuberculostatic Activity of Pyrrolyl and Pyrazolinyl Podands [J].
Fedorova, O. V. ;
Ovchinnikova, I. G. ;
Kravchenko, M. A. ;
Skornyakov, S. N. ;
Rusinov, G. L. ;
Chupakhin, O. N. ;
Charushin, V. N. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (07) :946-957
[9]   Synthesis and tuberculostatic activity of podands with a dihydropyrimidine fragment [J].
Filatova, E. S. ;
Fedorova, O. V. ;
Titova, Yu. A. ;
Slepukhin, P. A. ;
Kravchenko, M. A. ;
Skornyakov, S. N. ;
Rusinov, G. L. ;
Charushin, V. N. .
RUSSIAN CHEMICAL BULLETIN, 2016, 65 (05) :1360-1364
[10]  
Fraley M. E., US Patent, Patent No. 7262199