An Improved Synthesis of 4,8,9,10-Tetraaryl-1,3-Diazaadamantanes

Synthesis of diversely substituted adamantanes as a new class of antimicrobial agent

“…The compounds 5a-m were characterized by IR, 1 H-NMR, and 13 C-NMR. Among these, the synthesis and their unambiguous chemical shift assignments of and 5a-m (except 5c, 5e, 5f, 5h, 5l) were already reported, and their spectral values were found to be in accord with the literature [16][17][18][19][20][21]; and hence the characterizations of remaining compounds 5c, 5e, 5f, 5h, 5l were included in the experimental section. However, the microbial screening of all these compounds was not reported in the literature and hence all of these compounds were synthesized.…”

“…Though the synthesis of 4,8,9,10-tetraaryl-1,3-diazatricyclo[3.3.1.1]decan-6-ones and its corresponding alcohols have been reported [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] for a limited number of derivatives, their biological significance is not yet explored and hence in the present work 4,8,9,10-tetraaryl-1,3-diazatricyclo[3.3.1.1]decan-6-ones were synthesized using the reports available in the literature [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30], which in turn reduced into 4,8,9,10-tetraaryl-1,3-diazatricyclo[3.3.1.1]decan-6-ols using NaBH 4 ; characterized using IR, 1 H NMR, 13 C NMR, and mass spectral data and then subjected to antimicrobial evaluation against various microbial strains and the results were discussed.…”

“…The products 6a-m were characterized by IR, 1 H-NMR, and 13 C-NMR. Though some of these derivatives were already reported [16][17][18][19][20][21]; their complete chemical shift assignments were not available and hence the characterizations of 6a-m were included in the experimental section.…”

4,8,9,10-Tetraphenyl-1,3-diazaadamantan-6-one acetone hemisolvate

“…The benzene layer was separated, washed thoroughly with water, and evaporated to yield the crude adamantanone. This was recrystallized from a 2:2:1 mixture of benzene, chloroform and acetone and the melting points were noted (Quast & Mu È ller, 1980;Jackman et al, 1982;Quast et al, 1982;Sivasubramanian et al, 1990;Jeyaraman et al, 1992). Colourless single crystals were obtained as transparent needles from a saturated solution of the title compound in chloroform, benzene and acetone, by slow evaporation at room temperature.…”

A 1H and 13C NMR study of 4,8,9,10‐tetraaryl‐1,3‐diazatricyclo[3.3.1.13,7]decan‐6‐ones

“…Quast and co-workers 9 made assignments of proton and carbon signals of these compounds by comparison with the bicyclic analogs but did not distinctly assign the signals of the aryl rings. Sivasubramanian et al 10 tentatively assigned proton chemical shift data of diazaadamantan-6-ones. In the present work, we employed both one-and two-dimensional (H,H-COSY, C,H-COSY, NOESY, ROESY and HMBC) NMR techniques to assign unambiguously all proton and carbon resonances of a series of substituted 4,8,9,10-tetraaryl-1,3-diazatricyclo[3.3.1.1 3,7 ]decan-6-ones (1a-e) in order to (i) place the stereochemical deductions on a firm footing and (ii) examine the influence of the orientations of the phenyl rings on the chemical shifts of various proton and carbon nuclei in these molecules.…”