Synthesis of 4-Arylaminoquinazolines from 2-amino-N'-Arylbenzamidines and Orthoesters via the Dimroth Rearrangement of Intermediate Quinazolin-4(3H)- Imines

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:

• Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice,Poland

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.

Cite this article as:

Zemlak Krzysztof , Szczepankiewicz Wojciech *, Kula Bartłomiej and Bieg Tadeusz , Synthesis of 4-Arylaminoquinazolines from 2-amino-N'-Arylbenzamidines and Orthoesters via the Dimroth Rearrangement of Intermediate Quinazolin-4(3H)- Imines, Current Organic Chemistry 2018; 22 (28) . https://dx.doi.org/10.2174/1385272823666181126112958