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CC BY 4.0 · Synlett 2020; 31(15): 1507-1510
DOI: 10.1055/s-0040-1707080
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(2020) The Author(s)

2-Aminoquinazolines by Chan–Evans–Lam Coupling of Guanidines with (2-Formylphenyl)boronic Acids

Vitalii V. Solomin
a   Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, LV-1006, Latvia   Email: aigars@osi.lv
b   Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga LV-1048, Latvia
,
Alberts Seins
a   Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, LV-1006, Latvia   Email: aigars@osi.lv
b   Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga LV-1048, Latvia
,
Aigars Jirgensons  ∗
a   Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, LV-1006, Latvia   Email: aigars@osi.lv
b   Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga LV-1048, Latvia
› Author AffiliationsH2020 MSC-ITN project CARTNET “Combating Antimicrobial Resistance Training Network”, Grant agreement ID: 765147
Further Information

Publication History

Received: 30 April 2020

Accepted after revision: 10 June 2020

Publication Date:
08 July 2020 (online)

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Abstract

A new method is presented for the synthesis of 2-aminoquinazolines, which is based on a Chan–Evans–Lam coupling of (2-formylphenyl)boronic acids with guanidines. Relatively mild conditions involving the use of inexpensive CuI as a catalyst and methanol as a solvent permit the application of the method to a wide range of substrates. Nonsubstituted, N-monosubstituted, and N,N-disubstituted guanidines can be used as reactants to give the corresponding 2-aminoquinazolines in moderate yields from readily available (2-formylphenyl)boronic acids.

Key words

guanidines - Chan–Evans–Lam coupling - quinazolines - copper catalysis - formylphenylboronic acids

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707080.
  • Supporting Information
 

  • References and Notes

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