Issue 14, 2000

Heterocalixarenes Part 4. Synthesis of oxocalix[1]heterocycle[2]arenes: a unique H-bonding network in calix[1]benzimidazol-2-one[2]arene· 1/2H2O

Abstract

The Friedel–Crafts aroylation of 2-methylanisole with 3-methylbenzoyl chloride followed by NBS bromination and cyclizations with 1,3-dihydrobenzimidazol-2-one, 1,3-dihydro-5,6-dinitrobenzimidazol-2-one, uracil, 6-methyluracil and quinazoline-2,4(1H,3H)-dione provide respective oxocalix[1]heterocycle[2]arenes 5–9. The X-ray crystal structure (solid) and 1H NMR spectral (solution) studies show them to have by and large inwardly flattened partial cone conformations which vary in torsion angles between the rings. The calix[1]benzimidazol-2-one[2]arene·½ H2O complex shows a unique array of H-bonds in which three of the four CH and the imide oxygen of the benzimidazol-2-one unit, carbonyl oxygen and water molecule are involved in H-bonding with surrounding calixarene molecules. This heterocalixarene, in contrast to earlier reported benzimidazol-2-one-based calixarenes, does not show heterocyclic π–π stacking.

Supplementary files

Article information

Article type
Paper
Submitted
31 Jan 2000
Accepted
02 May 2000
First published
03 Jul 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2295-2301

Heterocalixarenes Part 4. Synthesis of oxocalix[1]heterocycle[2]arenes: a unique H-bonding network in calix[1]benzimidazol-2-one[2]arene· 1//2 H2O

S. Kumar, G. Hundal, D. Paul, M. S. Hundal and H. Singh, J. Chem. Soc., Perkin Trans. 1, 2000, 2295 DOI: 10.1039/B000832J

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