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Reaction of 5-Substituted 2-(3-Chloropropanoylamino)benzophenone syn- and anti-Oximes with Sodium Hydroxide

“…The IR spectra of syn isomers XI and XII contain stretching absorption bands of the hydroxyl group (354533550 cm 31 ), amide N3H bond (339533405, 327533285 cm 31 ), amide carbonyl group (16803 1685 cm 31 ), and azomethine bond (1605 cm 31 ); the respective bands of anti isomers XIII3XV are at 3545, 324533255, 167531685, and 160031605 cm 31 . Rely-ing on data in[9,10], we can suggest that anti isomers XIII3XV have an intramolecular hydrogen bond…”

“…The latter were refined in terms of the solid body model. Compounds I3V were synthesized as described in [9]. -2-(3-chloropropanoylamino)benzophenone anti-oxime (VIII).…”

“…Previously we reported the synthesis and structure of the syn and anti isomers of 2-(3-chloropropanoylamino)-5-methylbenzophenone (3-chloropropanoyl)oximines, possible building blocks for 18-membered dibenzodioxatetraaza macrocycles [9]. Proceeding with this research, we synthesized a series of syn and anti isomers of 3-(chloropropanoyl)oximines of 5-substituted 2-(3-chloropropanoylamino)benzophenones I3V whose aminolysis gave the corresponding syn and anti-oximes of 5-substituted 2-(3-chloropropanoylamino)benzophenones VI3X.…”

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

“…The FAB mass spectrum shows a strong peak for the [M+H] + ions with maximum intensity as well as fragmentation ions 295 (27.2%) and 277 (20.0%). In previous work [3], we showed that bands at 3390-3400 cm -1 corresponding to the NH bond of the free amide group are characteristic for the IR spectra of syn isomers of acyl derivatives of oximes, while these bands are lacking in the IR spectra of the corresponding anti isomers. The absence of a band in the IR spectrum of 2 in the region characteristic for the syn isomers suggests that the diacyl derivative of oxime 2 is an anti isomer.…”

“…The absence of a band in the IR spectrum of 2 in the region characteristic for the syn isomers suggests that the diacyl derivative of oxime 2 is an anti isomer. The isomerization of 2 during the acylation may be attributed to the acidic reaction medium (by analogy to the isomerization of the syn isomers of oximes of 2-aminobenzophenones upon their acylation by 3-chloropropionyl chloride in the absence of base [3]). We have already studied the structure of several quinazoline 3-oxides [11].…”