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

Abstract

In the title compound, C32H28N2O·0.5C3H6O, the two axial and two equatorial phenyl substituents are essentially planar. There are no hydrogen‐bonded interactions between the two independent mol­ecules in the asymmetric unit. The crystal packing is characterized by C—H⋯O interactions. The solvent (acetone) mol­ecule in the crystal structure significantly influences the packing, features of which are distinctly different from those of unsolvated 4,8,9,10‐tetra­phenyl‐1,3‐di­aza­adamantan‐6‐one and its methoxy‐ and chloro‐substituted analogues.

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

“…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 doublet at d 7.45 ppm and d 7.56 and integrating for four protons each with an coupling constant of8.4 Hz is due to the aryl protons at H-8c, 9c, 8c 0 , 9c 0 and H-8b, 9b, 8b 0 , 9b 0 .Carbon chemical shift assignment: The 13 C NMR spectrum reveals that the signal at d 49.90 ppm corresponds to the carbons at C-5, 7 and the signal at d 68.48 ppm corresponds to carbons at C-8, 9 respectively and the signal at d 63.40 ppm corresponds to the carbons at C-4 and C-10 respectively. The signal at d 67.94 ppm corresponds to the carbon at C-2 and the signal at d 211.90 ppm corresponds to carbon at C-6 respectively and the rest of the signals appears at 132 28. (ipso), 130.37 (ipso 0 ), 137.94 (para), 160.38, 136.23 (para 0 ), 129.50 (ortho), 128.39 (ortho 0 ), 121.80 (meta), 120.67 (meta 0 ).…”