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
Current Organic Chemistry
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.
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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
DOI https://dx.doi.org/10.2174/1385272823666181126112958 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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