Experimental and theoretical investigation of substituent effects in a two-pathway reaction of tetrahydro-1,5-benzodiazepine-2-thiones with 4-substituted 2-bromoacetophenones

Dihydroquinazolino[3,2‐a][1,5]benzodiazepines: Synthesis and Computational Study of Reductive N‐Heterocyclization of N‐(2‐Nitrobenzoyl)‐1,5‐benzodiazepin‐2‐ones

“…The Fukui function is a local reactivity descriptor that indicates the best way to change the number of electrons in a molecule. Hence, it indicates the propensity of the electronic density to deform at a given position, that is, to accept or donate electrons . With the aim of estimating the outcome of the reductive cyclization progress, we calculated the condensed Fukui function for nucleophilic attack [f + (r)] and electrophilic attack [f – (r)], and the frontier orbital π electron population on the particular atoms C2 and N‐C2′ of intermediates IIIa–j (Table ).…”

“…Following our previous studies on the construction of polycyclic compounds containing different heterocyclic rings annelated to the basic 1,5-benzodiazepine bicyclic system ( [1,3]thiazolo[3,2-a] [1,5]benzodiazepines [7], [1,2,4] oxadiazolo [4,3-a] [1,5]benzodiazepines [8], [1,4]diazepino [3,2,1-hi]pyrido [4,3,2-cd]indoles, and [1,4]diazepino [2,3-g] quinolines [9]), we planned the preparation of some quinazolino [1,5]benzodiazepines. Several examples of the synthesis of such combined heterocyclic rings, where the quinazoline nucleus is fused at different positions of the 1,5-benzodiazepine skeleton, have been reported [10,11].…”

The Bonding Nature of Cyclometalated Ru Complex: How DFT Study Revealing the Dewar‐Chatt‐Duncanson Model Relates to the Molecular Properties

“…The B3LYP is the most popular density functional [32,33] that yields quite suitable structural properties in the studies of metal catalyzed organic reactions and heterocyclic molecules. [34][35][36][37][38][39][40][41] The functional M06 [42,43] was shown to give good predictions of geometric parameters in organometallic compounds. [44] Therefore, different exchange-correlation density functionals were employed: BLYP, BP86, hybrid B3LYP, which are combinations of Beche (B) [45] Lee-Yang-Parr (LYP) [46] and Perdew'86 (P86), [47] Beche's three parameters (B3) [33] functionals and meta-hybrid M06 functional.…”

A combined experimental and theoretical study of the synthesis of quinazolino[3,2-a][1,5]benzodiazepin-13-ones

“…The molecular ESP charges on the molecular electron density iso-surface are a good indicator for the interpretation of chemical reactivity. [25][26][27]29 Hence, it gives a suitable description of molecular properties, such as strong noncovalent interactions that are predominantly electrostatic in nature. In our earlier quantum chemical reactivity descriptors studies of the substituted 1,5-benzodiazepine-2-thiones interaction with bromoketones, the performance of the AM1 method and DFT B3LYP functional with two different basis sets (6-31G* and 6-31+G*) was compared and it was stated that both methods provided very similar results.…”

“…In our earlier quantum chemical reactivity descriptors studies of the substituted 1,5-benzodiazepine-2-thiones interaction with bromoketones, the performance of the AM1 method and DFT B3LYP functional with two different basis sets (6-31G* and 6-31+G*) was compared and it was stated that both methods provided very similar results. 29 The advantage of the AM1 model is that it is less time consuming. However, the DFT B3LYP model allows the calculation of more molecular quantum properties, offers better accuracy in the estimation of reactivity descriptors, ensures high reliability, and includes a broader diversity of descriptors.…”