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, Tadeusz Bieg.

Journal Name: Current Organic Chemistry

Volume 22 , Issue 28 , 2018

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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.

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Article Details

VOLUME: 22
ISSUE: 28
Year: 2018
Page: [2801 - 2808]
Pages: 8
DOI: 10.2174/1385272823666181126112958
Price: $58

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