Synthesis of {2,3-Dihydro-7-halopyrrolo-[(2,1-b)]-quinazolin-9-(1H)-one and 2,3-Dihydro-5,7-dihalopyrrolo-[(2,1-b)]-quinazolin-9-(1H)-one}: New Analogs of Deoxyvasicinone

Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

“…13 C­{ 1 H} NMR (75 MHz, chloroform- d ) δ 160.0, 159.9, 147.7, 134.6, 132.0, 128.5, 125.8, 121.6, 46.7, 32.6, 19.6. NMR spectra are in accordance to the literature data…”

Extending the biocatalytic scope of regiocomplementary flavin-dependent halogenase enzymes

“…Interestingly, non-enzymatic halogenation of anthranilates using traditional chemistry favours C5 over C3, and can oen result in mixtures including C3 and C5 disubstituted products. 40,41 We do not observe any dihalogenation of 3 or 4 with the halogenases. Moreover the fact PrnA predominately halogenates anthranilic acid at C3, whilst the C5 position para to the activating amino group is intrinsically the most reactive position, 40,41 suggests that substrate binding still governs regioselectivity.…”

“…40,41 We do not observe any dihalogenation of 3 or 4 with the halogenases. Moreover the fact PrnA predominately halogenates anthranilic acid at C3, whilst the C5 position para to the activating amino group is intrinsically the most reactive position, 40,41 suggests that substrate binding still governs regioselectivity. Presumably while anthranilate (4) may have greater exibility in the PrnA active site, compared with the native substrate (Trp), it is preferentially bound in an orientation that would position C3 closer to the catalytic amino and carboxyl groups of K79 and E346 respectively.…”

Spectroscopic, DFT, and XRD Studies of Hydrogen Bonds in N-Unsubstituted 2-Aminobenzamides

“…2-Amino-5-bromobenzamide ( ABB ) [ 19 ], 2-amino-5-iodobenzamide ( AIB ) [ 20 ], 2-amino-3,5-dibromobenzamide ( ABBB ) [ 21 , 22 , 23 ], and 2-amino-5-bromo-3-iodobenzamide ( ABIB ) [ 24 ] were previously prepared from the commercially available 2-aminobenzamide ( AB ) as depicted in Scheme 1 .…”

“…Despite the enormous pharmacological [ 11 , 12 , 13 , 15 , 16 , 17 ] and chemical [ 19 , 20 , 21 , 22 , 23 , 24 ] interest in the N -unsubstituted 2-aminobenzamides, to our knowledge, the presence of intramolecular hydrogen bonding in these compounds has been less demonstrated in the literature [ 25 , 26 , 27 , 28 ]. This prompted us to study the structural properties of the known 5-bromo/iodo- and 3,5-dihalogenated 2-aminobezamides by means of spectroscopic (NMR, UV-Vis, IR, Raman) methods and single X-ray crystallography in combination with density functional theory methods.…”