ChemInform Abstract: NEW 2‐MONOALKYLAMINO AND 2‐DIALKYLAMINO‐4‐PHENYL‐3H‐1,5‐BENZODIAZEPINE

Abstract

Die Methylthio‐benzodiazepine (I) reagieren mit Aminen (II) zu den Amino‐benzodiazepinen (III), deren Umsetzung mit Salzsäure die Benzodiazepinone (IV) und in manchen Fällen das Benzimidazol (V) liefert.

Synthesis and tautomerism of 2-phenacyl-1H-benzimidazoles and their hydrogen bromide salts

“…The 1 H NMR spectra were taken at 20°C and the HMBC two-dimensional heteronuclear correlation spectrum was taken at 40°C on a Bruker Avance DRX 500 spectrometer at 500 and 125 MHz for solutions in DMSO-d 6 with the signal of the residual solvent protons as the internal standard. The semiempirical quantum-chemical calculations were carried out using the MOPAC program [23] with consideration of the effect of the medium using the COSMO model [24].…”

“…Tajana et al [6] have reported the synthesis of compound 1a by recyclization upon the acid hydrolysis of 2-(4-methylpiperazin-1-yl)-4-phenyl-1,5-benzodiazepine. Sakamoto et al [7] have reported the synthesis of compound 1i by the C-acylation of 2-methylbenzimidazole using 4-nitrobenzoyl cyanide.…”

Tautomeric Equilibria in Solutions of 2-Phenacylbenzimidazoles

“…2-Phenacylbenzimidazoles can be obtained by a variety of methods [5][6][7][8][9][10][11][12][13]. The aforementioned syntheses are characterized by low yield; therefore, 2-phenacylbenzimidazoles were prepared by treating methylbenzimidazole 1 with benzoyl chlorides in the presence of triethylamine followed by thermal decomposition of formed (Z)-2-(1-benzoyl-1H-benzo[d]imidazol-2-yl)-1-phenylvinyl benzoates 2a-i (Scheme 2) [5,7,11].…”

“…Light yellow solid; yield 1.22 g (87%); mp 182-183 ∘ C (lit. 176-178 [22], 179 [6], 178-178.5 [7], 178-179 ∘ C [4]); 1 H NMR (DMSO-d 6 from TMS) 4.68 (2H, s, CH 2 CO (K)), 6.10 (1H, s, CHO (O)), 7.17 (3H, m (O)), 7.42 (1H, m (O)), 7.45 7 (2H, m (O)), 7.49 (1H, m (K)), 7.57 (5H, m (K)), 7.68 (1H, m (K)), 7.86 (2H, m (O)), 8. 09 (2H, m (K)), 12.27 (1H, s, NH (O)), 12.34 (1H, s, NH (K)).…”

On benzo[b][1,4]diazepinium-olates, -thiolates and -carboxylates as anti-Hückel mesomeric betaines

“…In addition to this, benzo [b] [1,4]diazepines form a class of ongoing interest both from a chemical and a biological point of view. Thus, depending on the substitution pattern this ring system displays physiological effects as tranquilizers 16 or antidepressant agents. 17 Some derivatives act as depressants of the central nervous system and anticonvulsants, whereas others act as stimulants of the central nervous system and convulsants.…”