Synthesis, crystal and molecular structure of 2-(3-chloropropyl)-6-methyl-4-phenylquinazoline 3-oxide

Abstract

Keywords: quinazoline, mass spectrometry, X-ray diffraction structural analysis.The acylation of oximes of 2-aminobenzophenones with different agents such as chloroacetyl chloride and 3-chloropropionyl chloride holds interest since the acyl derivatives, as shown in our previous work [1-3], are valuable intermediates for the synthesis of 16-and 18-membered dibenzodioxatetraazamacroheterocycles. In our attempt to obtain intermediates for the synthesis of 20-membered macroheterocycles, we studied the acylation of the syn isomer of the oxime of 2-amino-5-methylbenzophenone (1) using 4-chlorobutyryl chloride and found that, in the absence of base and in the presence of excess acylating agent, 2-(3-chloropropyl)-6-methyl-4-phenylquinazoline 3-oxide (3) was found in addition to the anti isomer of the 4-chlorobutyryloximine of 2-(4-chlorobutyryl)amino-5-methylbenzophenone (2). NH 2 Ph Me N OH Cl O Cl N N Me Ph Cl O O Cl NH Ph Me O N O Cl + 1 2 3 __________________________________________________________________________________________ A. B. Bogatsky Physico-