Reaction of trifluoromethyl-containing 1,3-dicarbonyl compounds with bis-hydrazides

被引:5
作者
Zerov, A. V. [1 ]
Krupenya, T. S. [1 ]
Petrov, A. A. [1 ]
Yakimovich, S. I. [1 ]
机构
[1] St Petersburg State Univ, Univ Skii Pr 26, St Petersburg 198504, Russia
关键词
TAUTOMERISM; INHIBITORS; KETONES; SERIES;
D O I
10.1134/S1070428016030039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carbonic dihydrazide reacted with 2 equiv of trifluoroacetylacetone to give a compound containing 5-hydroxy-4,5-dihydropyrazole and keto enehydrazine fragments. Analogous 2 : 1 condensations of trifluoro-acetylacetone and 4-ethoxy-1,1,1-trifluorobut-3-en-2-one with oxalohydrazide and malonohydrazide afforded bis(5-hydroxy-4,5-dihydropyrazole) structures as two diastereoisomers.
引用
收藏
页码:312 / 318
页数:7
相关论文
共 15 条
[1]   New trifluoromethyl-containing (E)-N′-arylidene-[3-alkyl(aryl/heteroaryl)-4,5-dihydro-1H-pyrazol-1-yl]carbohydrazides: Synthesis, crystal structure and antimicrobial/antioxidant activity [J].
Bonacorso, Helio G. ;
Cavinatto, Susiane ;
Campos, Patrick T. ;
Porte, Liliane M. F. ;
Navarini, Jussara ;
Paim, Gisele R. ;
Martins, Marcos A. P. ;
Zanatta, Nilo ;
Stuker, Caroline Z. .
JOURNAL OF FLUORINE CHEMISTRY, 2012, 135 :303-314
[2]   An efficient and regioselective synthesis of 1,1′-oxalylbis[3-(alkyl/aryl/heteroaryl)-5-(trihalomethyl)-1H-pyrazoles] from 4-alkoxy-1,1,1-trihaloalk-3-en-2-ones [J].
Bonacorso, Helio G. ;
Cechinel, Cleber A. ;
Navarini, Jussara ;
Andrighetto, Rosalia ;
Martins, Marcos A. P. ;
Zanatta, Nilo .
MONATSHEFTE FUR CHEMIE, 2011, 142 (03) :277-285
[3]   β-Alkoxyvinyl trifluoromethyl ketones as efficient precursors for the one-pot synthesis of bis-(4,5-dihydro-1H-pyrazol-1-yl)methanones and 1H-pyrazolyl-1-carbohydrazides [J].
Bonacorso, Helio G. ;
Cechinel, Cleber A. ;
Deon, Everton D. ;
Sehnem, Ronan C. ;
Luz, Fabio M. ;
Martins, Marcos A. P. ;
Zanatta, Nilo .
ARKIVOC, 2009, :174-182
[4]   Regioselectively controlled synthesis of 3(5)-(trifluoromethyl) pyrazolylbenzenesulfonamides and their effects on a pathological pain model in mice [J].
Lobo, Marcio M. ;
Oliveira, Sara M. ;
Brusco, Indiara ;
Machado, Pablo ;
Timmers, Luis F. S. M. ;
de Souza, Osmar N. ;
Martins, Marcos A. P. ;
Bonacorso, Helio G. ;
dos Santos, Josiane M. ;
Canova, Bruna ;
da Silva, Thiago V. F. ;
Zanatta, Nilo .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 102 :143-152
[5]   Synthesis and structure of novel 4,5-dihydro-1H-pyrazoles:: salicylic acid based analgesic agents [J].
Machado, Pablo ;
Rosa, Fernanda A. ;
Rossatto, Marcelo ;
Sant'Anna, Gabriela da S. ;
Sauzem, Patricia D. ;
da Silva, Rubia M. Siqueira ;
Rubin, Maribel A. ;
Ferreira, Juliano ;
Bonacorso, Helio G. ;
Zanatta, Nilo ;
Martinsa, Marcos A. P. .
ARKIVOC, 2007, :281-297
[6]   Reaction of β-alkoxyvinyl halomethyl ketones with cyanoacetohydrazide [J].
Martins, Marcos A. P. ;
Moreira, Dayse N. ;
Frizzo, Clarissa P. ;
Longhi, Kelvis ;
Zanatta, Nilo ;
Bonacorso, Helio G. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2008, 19 (07) :1361-1368
[7]   An efficient synthesis of 1-cyanoacetyl-5-halomethyl-4,5-dihydro-1H-pyrazoles in ionic liquid [J].
Moreira, Dayse N. ;
Frizzo, Clarissa P. ;
Longhi, Kelvis ;
Zanatta, Nilo ;
Bonacorso, Helio G. ;
Martins, Marcos A. P. .
MONATSHEFTE FUR CHEMIE, 2008, 139 (09) :1049-1054
[8]   Reaction of aroyl- and hetaroyltrifluoroacetones with acylhydrazines: Regioselectivity and tautomerism of the condensation products [J].
Pakal'nis, V. V. ;
Zerova, I. V. ;
Yakimovich, S. I. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2007, 77 (10) :1732-1741
[9]  
Pakalnis V. V., 2009, VESTN SANKT PETERB 4, V4, P78
[10]   High-Throughput Virtual Screening Identifies Novel N′-(1-Phenylethylidene)-benzohydrazides as Potent, Specific, and Reversible LSD1 Inhibitors [J].
Sorna, Venkataswamy ;
Theisen, Emily R. ;
Stephens, Bret ;
Warner, Steven L. ;
Bearss, David J. ;
Vankayalapati, Hariprasad ;
Sharma, Sunil .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (23) :9496-9508