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Tandem transformations of nitriles into N-heterocyclic compounds by electrophilic trapping of Blaise reaction intermediates

Title
Tandem transformations of nitriles into N-heterocyclic compounds by electrophilic trapping of Blaise reaction intermediates
Authors
Kim J.Chun Y.Shin H.Lee S.-G.
Ewha Authors
이상기김주현
SCOPUS Author ID
이상기scopus
Issue Date
2012
Journal Title
Synthesis (Germany)
ISSN
0039-7881JCR Link
Citation
vol. 44, no. 12, pp. 1809 - 1817
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Tandem transformations of nitriles into various N-heterocycles have been accomplished through the reaction of electrophiles with Blaise reaction intermediates formed in situ. The reaction of the Blaise reaction intermediates with propiolates gives 2-pyridones through consecutive C- and N-nucleophilic reactions. The tandem reactions of the Blaise reaction intermediate with 1,3-enynes proceed through C-nucleophilic addition followed by an electrocyclization-aromatization cascade to give pyridines. Exocyclic enamino esters can be prepared by transformations of ω-chloroalkyl nitriles through chemoselective intramolecular alkylation of the Blaise reaction intermediate. Palladium-catalyzed intramolecular arylations or copper-catalyzed intermolecular cross-coupling reactions of the Blaise reaction intermediate give a range of indole derivatives. Combinations of tandem alkylations and palladium-catalyzed couplings of the Blaise reaction intermediates of ω-chloroalkyl nitriles give N-fused indoles. © Georg Thieme Verlag Stuttgart · New York.
DOI
10.1055/s-0031-1290814
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자연과학대학 > 화학·나노과학전공 > Journal papers
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