Preparation of 1,2,5-Trisubstituted 1H-Imidazoles from Ketenimines and Prop­arg­ylic Amines by Silver-Catalyzed or Iodine-Promoted Electrophilic Cyclization Reaction of Alkynes

2015 ◽  
Vol 2015 (26) ◽  
pp. 5789-5797 ◽  
Author(s):  
Xiaorong Zhou ◽  
Zheng Jiang ◽  
Lexing Xue ◽  
Ping Lu ◽  
Yanguang Wang
Keyword(s):  
Cyclization Reaction ◽  
Electrophilic Cyclization

Synthesis of Novel Bis-pyrazoles via Electrophilic Cyclization

2019 ◽  
Vol 16 (6) ◽  
pp. 511-516
Author(s):  
Adnan Cetin
Keyword(s):  
13C Nmr ◽  
Cyclization Reaction ◽  
Electrophilic Cyclization ◽  
Pyrazole Derivatives ◽  
Spectral Analyses ◽  
Mass Spectral ◽  
Palladium Catalyzed ◽  
Ft Ir ◽  
Reaction Compound

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.

Iodine-mediated regioselective 5-endo-dig electrophilic cyclization reaction of selenoenynes: synthesis of selenophene derivatives

2017 ◽  
Vol 4 (2) ◽  
pp. 277-282 ◽  
Author(s):  
Renan P. Pistoia ◽  
Juliano A. Roehrs ◽  
Davi F. Back ◽  
Gilson Zeni
Keyword(s):  
Cyclization Reaction ◽  
Electrophilic Cyclization ◽  
Cyclization Reactions

Selenoenynes underwent electrophilic cyclization reactions with iodine in the presence of an appropriate nucleophile to give 3-iodo-selenophenes and 3-organoselenyl-selenophenes.

Electrophilic cyclization of an olefinic β-keto ester

1981 ◽  
Vol 59 (14) ◽  
pp. 2239-2241 ◽  
Author(s):  
Margot Alderdice ◽  
Larry Weiler
Keyword(s):  
Silica Gel ◽  
Aluminum Chloride ◽  
Cyclization Reaction ◽  
Electrophilic Cyclization ◽  
Keto Ester ◽  
Potential Use

Benzeneselenenyl chloride and aluminum chloride or benzenesulphenyl chloride and silica gel initiate an electrophilic cyclization of methyl 7-methyl-3-oxo-7-octenoate to cyclohexyl derivatives. These products of the cyclization reaction have been converted into intermediates of potential use in the synthesis of unusual carotenoids.

Synthesis of Organochalcogen Propargyl Aryl Ethers and Their Application in the Electrophilic Cyclization Reaction: An Efficient Preparation of 3-Halo-4-Chalcogen-2H-Benzopyrans

2009 ◽  
Vol 74 (9) ◽  
pp. 3469-3477 ◽  
Author(s):  
Benhur Godoi ◽  
Adriane Sperança ◽  
Davi F. Back ◽  
Ricardo Brandão ◽  
Cristina W. Nogueira ◽  
...  
Keyword(s):  
Cyclization Reaction ◽  
Electrophilic Cyclization ◽  
Aryl Ethers

Synthesis of 3-Halo-7-azaindoles through a 5-endo-dig Electrophilic Cyclization Reaction

Synlett ◽  
2019 ◽  
Vol 30 (10) ◽  
pp. 1246-1252 ◽  
Author(s):  
Aimee Philips ◽  
Christopher Cunningham ◽  
Kajal Naran ◽  
Tanay Kesharwani
Keyword(s):  
Sodium Chloride ◽  
Molecular Iodine ◽  
Cyclization Reaction ◽  
Sodium Bromide ◽  
Environmentally Benign ◽  
Electrophilic Cyclization ◽  
Reaction Conditions ◽  
High Yields ◽  
Simple Atom

Biologically useful 7-azaindoles were synthesized by electrophilic cyclization of 3-alkynyl-N,N-dimethylpyridine-2-amines with molecular iodine. By this simple atom-economical approach under ambient reaction conditions, a library of interesting 3-iodo-7-azaindoles were synthesized in high yields. To synthesize the corresponding 3-bromo- and 3-chloro-7-azaindoles, an environmentally benign copper-mediated cyclization was employed, with inexpensive, nontoxic, and noncorrosive sodium chloride and sodium bromide as the sources of chlorine and bromine, respectively.

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