scholarly journals Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach

2014 ◽  
Vol 10 ◽  
pp. 1759-1764 ◽  
Author(s):  
Barbara Palka ◽  
Angela Di Capua ◽  
Maurizio Anzini ◽  
Gyté Vilkauskaité ◽  
Algirdas Šačkus ◽  
...  
Keyword(s):  
Multicomponent Reaction ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
One Pot ◽  
Silver Triflate ◽  
Microwave Assisted ◽  
Spectroscopic Investigations ◽  
Coupling Conditions ◽  
Substituted 1

A straightforward synthesis of 6-substituted 1-phenyl-3-trifluoromethyl-1H-pyrazolo[4,3-c]pyridines and the corresponding 5-oxides is presented. Hence, microwave-assisted treatment of 5-chloro-1-phenyl-3-trifluoromethylpyrazole-4-carbaldehyde with various terminal alkynes in the presence of tert-butylamine under Sonogashira-type cross-coupling conditions affords the former title compounds in a one-pot multicomponent procedure. Oximes derived from (intermediate) 5-alkynyl-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehydes were transformed into the corresponding 1H-pyrazolo[4,3-c]pyridine 5-oxides by silver triflate-catalyzed cyclization. Detailed NMR spectroscopic investigations (1H, 13C, 15N and 19F) were undertaken with all obtained products.

scholarly journals Dipyrazolo[1,5-a:4',3'-c]pyridines – a new heterocyclic system accessed via multicomponent reaction

2012 ◽  
Vol 8 ◽  
pp. 2223-2229 ◽  
Author(s):  
Wolfgang Holzer ◽  
Gytė Vilkauskaitė ◽  
Eglė Arbačiauskienė ◽  
Algirdas Šačkus
Keyword(s):  
Hydrogen Atom ◽  
Multicomponent Reaction ◽  
Heterocyclic System ◽  
Silver Triflate ◽  
Spectroscopic Investigations ◽  
Tricyclic Compounds

The synthesis of dipyrazolo[1,5-a:4',3'-c]pyridines is described. Easily obtainable 5-alkynylpyrazole-4-carbaldehydes, p-toluenesulfonyl hydrazide, and an aldehyde or ketone containing an α-hydrogen atom were reacted in a silver triflate catalyzed multicomponent reaction affording new tricyclic compounds with a dipyrazolo[1,5-a:4',3'-c]pyridine core. Detailed NMR spectroscopic investigations (1H, 13C and 15N) were undertaken with all obtained compounds.

Synthesis of seven-membered heterocycles via copper-catalyzed cross-coupling of terminal alkynes with diazo compounds and sequential Michael addition

2017 ◽  
Vol 15 (25) ◽  
pp. 5272-5274 ◽  
Author(s):  
Shenghu Yan ◽  
Shengyu Cao ◽  
Jiangtao Sun
Keyword(s):  
Michael Addition ◽  
Cross Coupling ◽  
Diazo Compounds ◽  
Terminal Alkynes ◽  
One Pot ◽  
Novel Approach

A novel approach to synthesize seven-membered heterocycles is established by reacting amide tethered terminal alkynes with aryl diazoacetates in a one-pot reaction.

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