Stereoselective Synthesis of 3-Alkylideneoxindoles by Palladium-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Organoboron Reagents

2008 ◽  
Vol 10 (21) ◽  
pp. 4887-4889 ◽  
Author(s):  
Tomoya Miura ◽  
Takeharu Toyoshima ◽  
Yusuke Takahashi ◽  
Masahiro Murakami
2009 ◽  
Vol 11 (10) ◽  
pp. 2141-2143 ◽  
Author(s):  
Tomoya Miura ◽  
Takeharu Toyoshima ◽  
Yusuke Takahashi ◽  
Masahiro Murakami

2019 ◽  
Vol 16 (6) ◽  
pp. 511-516
Author(s):  
Adnan Cetin

Efficient steps towards the synthesis of novel (phenyl)(1'-aryl-1,5,5'-triphenyl[3,3'-bi-1Hpyrazol]- 4-yl)methanones 4a-e were developed. The procedure starts from 1-(4-benzoyl-1,5-diphenyl- 1H-3-pyrazolyl)-3-phenyl-2-propyn-1-one (2) which was synthesized by a palladium catalyzed crosscoupling reaction. Compound 2 reacted with various hydrazines to give (E)-(phenyl)[1,5-diphenyl-3- [3-phenyl-1-(2-arylhydrazono)-2-propyn-1-yl]-1H-4-pyrazolyl]methanones E-3a-e. The bis-pyrazole derivatives 4a-e were synthesized from electrophilic cyclization reaction of α,β-acetylenic hydrazones E-3a-e and copper(I) iodide. All synthesized compounds were characterized by FT-IR, 1H, 13C NMR and Mass spectral analyses.


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