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

[ Vol. 22 , Issue. 28 ]

Author(s):

Krzysztof Zemlak, Wojciech Szczepankiewicz*, BartÅ‚omiej Kula and Tadeusz Bieg   Pages 2801 - 2808 ( 8 )

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.

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

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