title: 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.
abstract: 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.
authors.affiliation: Department of Chemistry and Nano Science (BK21), Ewha Womans University, 125-750 Seoul, Korea.
authors.forename: Ju Hyun
authors.initials: JH
authors.lastname: Kim
authors.forename: Hyunik
authors.initials: H
authors.lastname: Shin
authors.forename: Sang-gi
authors.initials: SG
authors.lastname: Lee
mesh_terms: D000478:Alkylation; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013379:Substrate Specificity
chemical_list: D004952:Esters; D006571:Heterocyclic Compounds