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 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 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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