9-phenyl-4,5,6,7,8,9-geksagidrotetrazolo[5,1-b]quinazoline in solution undergoes reaggregation ent via an azide to form a positional isomer corner structure that is installed involving spectral methods (1H-NMR, IR -spectra), TLC, chromato-mass spectrometry.
Temperature dependence of the 1H NMR spectra and TLC data suggest turning the corner isomers of о-сhlorоpheniltetrazolocyclanopyrimidine in the thermodynamically more stable linear forms. The IR spectra were recorded isomeric azide intermediate transformations.
To synthesize new potentially biologically active benzimidazoloquinazolines, a three-component condensation of 2-aminobenzimidazole, cyclohexanone and hydroxylatedbenzaldehydes was studied. The reaction proceeds regioselectively when the equimolar ratios of the reagents are boiled for 3 hours in N,N-dimethylformamide and is accompanied by the formation of ortho-phenyl substituted hexahydrobenz[4,5]imidazolo [1,2-a]quinazolines having an angular articulation of the rings and a different number and position of hydroxyl groups in the phenyl substituent.
The onе-pot interaction of C-aminotetrazole, cyclohexanone and o-R-benzaldehydes (in contrast to unsubstituted benzaldehyde benzaldehyde) leads to the formation of additionally linear tetrazohexahydroquinazolines, their isomers with an angular articulation of the rings. The appearance of isomers with angular articulation of the rings can be explained by the total influence of the spatial and electronic effects, and the influence of the low-energy interaction by the type of hydrogen binding NH ··R (VVS) can not be ruled out.
With three-component condensation of 1,2,4-triazol-3-amine, hydroxy-substituted aromatic aldehyde (2-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 2-naphthalene-carbaldehyde), cyclohexanone, the aldehyde component has a defining impact on the shaping of triazologic hydroquinazolines with different types of rings articulation and the position of the double bond in them (C4a–C5 and C4a–C8a).
Aryl-substituted triazolohexahydroquinazolines have been synthesized by means of three-component condensation of pnitro(pbromo) benzaldehydes, cyclohexanone, 1,2,4-triazol-3-amine. A scheme of the reaction mechanism is proposed, which makes it possible to explain the features of the behavior of p-nitro(bromo) benzaldehydes in condensation reactions in comparison with their ortho-substituted analogs.
