The Reaction of 2-(Acylamino)benzonitriles with Primary Aromatic Amines: A Convenient Synthesis of 2-Substituted 4-(Arylamino)quinazolines

Abstract

2-Substituted 4-(arylamino)quinazolines were prepared from 2-(acylamino)benzonitriles and primary arylamines by refluxing in either ethanol using trifluoroacetic acid as a catalyst or acetic acid. The 2-aminobenzonitrile was acylated by reaction with anhydrides, isocyanates, or ethyl chloroformate at room temperature.

Crystal structure of 3-(4-hydroxyphenyl)-2-[(E)-2-phenylethenyl]quinazolin-4(3H)-one

“…Compound 5 was obtained as a greyish solid. Its spectroscopic data corresponded to those in the literature (Marinho & Proença, 2015). The crude product 5, without further purification, was subjected to condensation with benzaldehyde analogously to a known method (Krastina et al, 2014): 3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)one (5) (0.276 g, 1.1 mmol), benzaldehyde (0.27 g, 2.53 mol) and acetanhydride (0.5 ml) in acetic acid (4 ml) were refluxed for 8 h, poured into crushed ice (50 ml), filtered and air-dried.…”

Microwave-Assisted Synthesis of Potential Bioactive Benzo-, Pyrido- or Pyrazino-thieno[3,2-d]pyrimidin-4-amine Analogs of MPC-6827

“…Microwave-assisted heating is an efficient technology that allows reproducible and safe operating conditions for convenient access to various molecules when traditional multistep processes would need long reaction times and unstable and toxic reagents (e.g., formamide and POCl 3 ) [ 21 , 22 , 23 , 24 ]. The innovative conditions previously described for the synthesis of MPC-6827 failed to provide compounds 4a–d and a more traditional approach was investigated.…”

One-Pot Reactions of Triethyl Orthoformate with Amines

“…Conventional heating methods are generally applied, as well as other strategies that include the use of efficient and more environmentally friendly catalysts, or microwave irradiation. The synthesis of quinazoline derivatives has also attracted great attention in recent years, and numerous synthetic procedures for their formation have been developed [38][39][40][41][42][43]. It is currently in numerous accepted drugs and biologically active compounds, like erlotinib, gefitinib, prazosin, rutaecarpine and many others, as well as in clinical candidates and biologically active molecules [44][45][46].…”