25654-24-4

Upstream product

• 6280-87-1 δ-chlorovaleronitrile 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 61486-97-3 ethyl 8-hydroxy-6-oxo-1,3,4,6-tetrahydro-2H-9-quinolizinecarboxylate 
• 164366-29-4 ethyl 4-oxo-6,7,8,9-tetrahydro-4H-quinolizine-1-carboxylate 
• 50620-95-6 4-methyl-2-o-tolyl-6,7,8,9-tetrahydro-2H-quinolizine-1,3-dicarboxylic acid diethyl ester 
• 1006381-23-2 C₁₈H₂₁NO₂ 
• 1256092-95-1 (Z)-ethyl 2-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-2-(piperidin-2-ylidene)acetate 
• 99834-45-4 2-Piperidin-(2Z)-ylidene-indan-1-one 
• 118268-56-7 ethyl 5-phenyl-2-(α-hexahydropyridylidene)-pentanoate 
• 118282-77-2 2-(4-phenylbutyl)-3,4,5,6-tetrahydropyridine 
• 96333-51-6 3-Phenyl-2-piperidin-(2Z)-ylidene-propionic acid ethyl ester 

Relevant academic research and scientific papers

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

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.

Chemoselective intramolecular alkylation of the Blaise reaction intermediates: Tandem one-pot synthesis of exo -cyclic enaminoesters and their applications toward the synthesis of N -heterocyclic compounds

The intramolecular alkylative reactivity and N/C selectivity of the various Blaise reaction intermediates, which are formed from the reaction of the Reformatsky reagents with ω-chloroalkyl nitriles, did not reach the synthetic potential as an entry to exo-cyclic enaminoesters. To circumvent this issue, various additives were investigated, among which the addition of NaHMDS dramatically enhanced the reactivity and N/C selectivity. This modification provided a highly efficient route for the synthesis of various N-fused heterocyclic compounds, as it requires only two steps from nitriles.