35150-22-2Relevant articles and documents
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Celerier,J.P. et al.
, p. 3089 (1979)
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Tandem transformations of nitriles into N-heterocyclic compounds by electrophilic trapping of Blaise reaction intermediates
Kim, Juhyun,Chun, Yusung,Shin, Hyunik,Lee, Sang-Gi
experimental part, p. 1809 - 1817 (2012/08/08)
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.
Silver-catalyzed hydroamination: Synthesis of N-bridgehead pyrroles, incorporating a protection-deprotection strategy for preparation of cyclic secondary vinylogous carbamates
Robinson, Ross S.,Dovey, Martin C.,Gravestock, David
, p. 505 - 511 (2007/10/03)
N-Bridgehead pyrroles are efficiently prepared from cyclic secondary vinylogous carbamates using a two-step sequence. This sequence involves C-propargylation followed by a silver-catalyzed intramolecular hydroamination. Hydroamination is brought about using microwave irradiation and affords the desired N-bridgehead pyrroles rapidly and in good yield. Cyclic secondary vinylogous carbamates are prepared using a mild, economical procedure. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
