Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Research Article

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

Author(s): Krzysztof Zemlak, Wojciech Szczepankiewicz*, Bartłomiej Kula and Tadeusz Bieg

Volume 22, Issue 28, 2018

Page: [2801 - 2808] Pages: 8

DOI: 10.2174/1385272823666181126112958

Price: $65

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.

Keywords: Quinazolinimines, quinazolines, Dimroth rearrangement, orthoformate, orthoacetate, orthopropionate, cyclization, 4- ethoxyquinazoline.

Graphical Abstract

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy