190274-01-2Relevant articles and documents
2-Aminoquinazolines by Chan-Evans-Lam Coupling of Guanidines with (2-Formylphenyl)boronic Acids
Solomin, Vitalii V.,Seins, Alberts,Jirgensons, Aigars
supporting information, p. 1507 - 1510 (2020/07/24)
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.
Discovery of novel aminoquinazolin-7-yl 6,7-dihydro-indol-4-ones as potent, selective inhibitors of heat shock protein 90
Huang, Kenneth H.,Barta, Thomas E.,Rice, John W.,Smith, Emilie D.,Ommen, Andy J.,Ma, Wei,Veal, James M.,Fadden, R. Patrick,Barabasz, Amy F.,Foley, Briana E.,Hughes, Philip F.,Hanson, Gunnar J.,Markworth, Christopher J.,Silinski, Melanie,Partridge, Jeffrey M.,Steed, Paul M.,Hall, Steven E.
scheme or table, p. 2550 - 2554 (2012/05/20)
A novel class of Hsp90 inhibitors, structurally distinct from previously reported scaffolds, was developed from rational design and optimization of a compound library screen hit. These aminoquinazoline derivatives, represented by compound 15 (SNX-6833) or 1-(2-amino-4-methylquinazolin-7-yl)-3,6,6-trimethyl-6, 7-dihydro-1H-indol-4(5H)-one, selectively bind to Hsp90 and inhibit its cellular activities at concentrations as low as single digit nanomolar.
Synthesis of 2-Aminoquinazolines from ortho-Fluorobenzaldehydes
Hynes, John B.,Campbell, Johnny P.
, p. 385 - 387 (2007/10/03)
The reaction of guanidine carbonate with various ortho-fluorobenzaldehydes in N,N-dimethylacetamide was investigated as a potential route for preparing 2-aminoquinazolines. Eleven new 2-aminoquinazolines were elaborated in this manner in low to moderate yields. In general the best results were obtained with ortho-fluorobenzaldehydes possessing an electron withdrawing substituent at the other ortho position. Complex mixtures were obtained using 2-fluorobenzaldehyde, 2,5-difluorobenzaldehyde and 2-fluoro-5-methoxybenzaldehyde which were not resolved.
