Synthesis of 4-arylaminoquinazolines from 2-amino-n'-arylbenzamidines and orthoesters via the dimroth rearrangement of intermediate quinazolin-4(3h)-imines

Krzysztof Zemlak; Wojciech Szczepankiewicz; Bartłomiej Kula; Tadeusz Bieg

doi:10.2174/1385272823666181126112958

Synthesis of 4-arylaminoquinazolines from 2-amino-n'-arylbenzamidines and orthoesters via the dimroth rearrangement of intermediate quinazolin-4(3h)-imines

Krzysztof Zemlak
, Wojciech Szczepankiewicz
, Bartłomiej Kula
, Tadeusz Bieg

Department of Organic Chemistry; Bioorganic Chemistry and Biotechnology (RCH/RCH2)

AMEplus Sp. Z O.o.

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2801-2808
Number of pages	8
Journal	Current Organic Chemistry
Volume	22
Issue number	28
DOIs	https://doi.org/10.2174/1385272823666181126112958
Publication status	Published - 2018

Keywords

4-ethoxyquinazoline
Cyclization
Dimroth rearrangement
Orthoacetate
Orthoformate
Orthopropionate
Quinazolines
Quinazolinimines

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.2174/1385272823666181126112958

Cite this

@article{ee6c7707f8a14f9d97a4d1d3eeae1360,

title = "Synthesis of 4-arylaminoquinazolines from 2-amino-n'-arylbenzamidines and orthoesters via the dimroth rearrangement of intermediate quinazolin-4(3h)-imines",

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 = "4-ethoxyquinazoline, Cyclization, Dimroth rearrangement, Orthoacetate, Orthoformate, Orthopropionate, Quinazolines, Quinazolinimines",

author = "Krzysztof Zemlak and Wojciech Szczepankiewicz and Bart{\l}omiej Kula and Tadeusz Bieg",

note = "Publisher Copyright: {\textcopyright} 2018 Bentham Science Publishers.",

year = "2018",

doi = "10.2174/1385272823666181126112958",

language = "English",

volume = "22",

pages = "2801--2808",

journal = "Current Organic Chemistry",

issn = "1385-2728",

publisher = "Bentham Science Publishers",

number = "28",

}

TY - JOUR

T1 - Synthesis of 4-arylaminoquinazolines from 2-amino-n'-arylbenzamidines and orthoesters via the dimroth rearrangement of intermediate quinazolin-4(3h)-imines

AU - Zemlak, Krzysztof

AU - Szczepankiewicz, Wojciech

AU - Kula, Bartłomiej

AU - Bieg, Tadeusz

PY - 2018

Y1 - 2018

N2 - 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.

AB - 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.

KW - 4-ethoxyquinazoline

KW - Cyclization

KW - Dimroth rearrangement

KW - Orthoacetate

KW - Orthoformate

KW - Orthopropionate

KW - Quinazolines

KW - Quinazolinimines

UR - https://www.scopus.com/pages/publications/85062045439

U2 - 10.2174/1385272823666181126112958

DO - 10.2174/1385272823666181126112958

M3 - Article

AN - SCOPUS:85062045439

SN - 1385-2728

VL - 22

SP - 2801

EP - 2808

JO - Current Organic Chemistry

JF - Current Organic Chemistry

IS - 28

ER -

Synthesis of 4-arylaminoquinazolines from 2-amino-n'-arylbenzamidines and orthoesters via the dimroth rearrangement of intermediate quinazolin-4(3h)-imines

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this