title: 1,3-Dipolar Cycloaddition in the Preparation of New Fused Heterocyclic Compounds via Thermal Initiation.
abstract: This paper describes the synthesis of precursors with a benzo[b]furan skeleton for the intramolecular 1,3-dipolar cycloaddition of azomethine ylides prepared from N-substituted 3-allyl-aminobenzo[b]furan-2-aldehydes and secondary amines derived from α-amino acid esters. Reactions were initiated by heating. The products consisted of four fused rings with three stereogenic centers. Their structure and stereochemistry were determined by NMR spectra and X-ray measurements.
authors: Department of Chemistry, Masaryk University, Kotlářská 2, Brno 611-37, Czech Republic. 380165@mail.muni.cz.
authors: Martin
authors: M
authors: Porubský
authors: Department of Chemistry, Masaryk University, Kotlářská 2, Brno 611-37, Czech Republic. 175258@mail.muni.cz.
authors: Lukáš
authors: L
authors: Tenora
authors: Department of Chemistry, Masaryk University, Kotlářská 2, Brno 611-37, Czech Republic. potacek@chemi.muni.cz.
authors: Milan
authors: M
authors: Potáček
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis; D001391:Azo Compounds / Q000737:chemistry; D061565:Cycloaddition Reaction; D005663:Furans / Q000138:chemical synthesis*; D006358:Hot Temperature; D008968:Molecular Conformation; D013882:Thiosemicarbazones / Q000737:chemistry
chemical_list: D000447:Aldehydes; D001391:Azo Compounds; D005663:Furans; D013882:Thiosemicarbazones; C512188:azomethine
keywords: 1,3-dipolar cycloaddition; 3-amino-benzo[b]furan-2-carbaldehyde; fused heterocycles; thermal initiation