title: Three-component reaction toward polyannulated quinazolinones, benzoxazinones, and benzothiazinones.
abstract: An efficient conversion of readily accessible cyclic imines with acid chlorides, that are able to take part in nucleophilic aromatic substitution (SNAr) reactions is realized in a new three-component, one-pot reaction, giving at least tricyclic annulated quinazolinones, benzoxazinones, and benzothiazinones as a result of the employed nitrogen, oxygen, or sulfur nucleophiles, respectively. Especially in the case of quinazolinones, this convenient strategy enables the access to heterocycles of heightened diversity, which offer the development of efficient derivatizations of the elaborated heterocyclic scaffolds. In a subsequent Heck or Ullmann cyclization, further annulations to the mentioned quinazolinones can be carried out.
authors.affiliation: Carl von Ossietzky Universität Oldenburg Fakultät für Mathematik und Naturwissenschaften Institut für Chemie Carl-von-Ossietzky-Strasse 9-11, 26129 Oldenburg, Deutschland.
authors.forename: Denis
authors.initials: D
authors.lastname: Kröger
authors.forename: Torben
authors.initials: T
authors.lastname: Schlüter
authors.forename: Malte
authors.initials: M
authors.lastname: Fischer
authors.forename: Irina
authors.initials: I
authors.lastname: Geibel
authors.forename: Jürgen
authors.initials: J
authors.lastname: Martens
mesh_terms: D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D052999:Quinazolinones / Q000138:chemical synthesis* / Q000737:chemistry; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D048588:Benzoxazines; D052999:Quinazolinones; D013843:Thiazines
keywords: Heck; Ullmann; cyclic imines; heterocycles; multicomponent reaction; polyannulation