Title:Synthesis of 4-Arylaminoquinazolines from 2-amino-N'-Arylbenzamidines and Orthoesters via the Dimroth Rearrangement of Intermediate Quinazolin-4(3H)- Imines
VOLUME: 22 ISSUE: 28
Author(s):Krzysztof Zemlak, Wojciech Szczepankiewicz*, Bartłomiej Kula and Tadeusz Bieg
Affiliation:Syntal Chemicals, Labedzka 59, 44-121 Gliwice, Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Syntal Chemicals, Labedzka 59, 44-121 Gliwice, Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice
Keywords:Quinazolinimines, quinazolines, Dimroth rearrangement, orthoformate, orthoacetate, orthopropionate, cyclization, 4-
ethoxyquinazoline.
Abstract:A reaction of 2-amino-N'-arylbenzamidines with triethyl
orthoformate, orthoacetate and orthopropionate leads to quinazolin-4(3H)-
imines. These compounds transform to 4-arylaminoquinazolines by heating in
acetic acid according to the Dimroth rearrangement mechanism. Unexpectedly,
these imines heated in ethanol gave mixtures of 4-arylaminoquinazolines and 4-
ethoxy-quinazoline.
