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

Vitalii V. Solomin; Alberts Seins; Aigars Jirgensons

doi:10.1055/s-0040-1707080

Synlett, Table of Contents

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

^aLatvian Institute of Organic Synthesis, Aizkraukles 21, Riga, LV-1006, Latvia Email: aigars@osi.lv

^bFaculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga LV-1048, Latvia

,

Alberts Seins

^aLatvian Institute of Organic Synthesis, Aizkraukles 21, Riga, LV-1006, Latvia Email: aigars@osi.lv

^bFaculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga LV-1048, Latvia

,

Aigars Jirgensons ∗

^aLatvian Institute of Organic Synthesis, Aizkraukles 21, Riga, LV-1006, Latvia Email: aigars@osi.lv

^bFaculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga LV-1048, Latvia

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Abstract

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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

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References

References and Notes
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