Heterocalixarenes Part 3: Bis-oxo-bridged calix[1]cyclicurea[3]arene and calix[1]cyclicurea[1]pyridine[2]arenes. Synthesis, X-ray crystal structure and conformational analysis

Subodh Kumar; Dharam Paul; Geeta Hundal; Maninder Singh Hundal; Harjit Singh

doi:10.1039/A906883J

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Heterocalixarenes Part 3: Bis-oxo-bridged calix[1]cyclicurea[3]arene and calix[1]cyclicurea[1]pyridine[2]arenes. Synthesis, X-ray crystal structure and conformational analysis¹

Subodh Kumar,*^a Dharam Paul,^a Geeta Hundal,^a Maninder Singh Hundal^a and Harjit Singh*^a

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* Corresponding authors

^a Department of Chemistry, Guru Nanak Dev University, Amritsar, India

Abstract

The Friedel–Crafts aroylations of 2- and 4-methylanisole with isophthaloyl dichloride or pyridine-2,6-dicarbonyl dichloride provide respective diones, which on bromination with NBS provide corresponding bisbromomethyl derivatives that undergo simple cyclocondensations with embedded cyclicurea-containing heterocycles, viz. benzimidazol-2(1H)-one, 5-nitrobenzimidazol-2(1H)-one, 5,6-dinitrobenzimidazol-2(1H)-one, uracil and quinazoline-2,4(1H,3H)-dione to form 11 new bis-oxo-bridged heterocalix[4]arenes (11–19, 24, 25). The X-ray crystal structure of the 11–benzene complex, ¹H–¹H COSY spectra and energy-minimization studies assign partial cone conformations to these heterocalix[4]arenes. The variation in the cyclicurea moiety controls the flexibility of these heterocalix[4]arenes.

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Crystal structure data TXT (22K)

Article information

DOI: https://doi.org/10.1039/A906883J
Article type: Paper
Submitted: 24 Aug 1999
Accepted: 19 Jan 2000
First published: 07 Mar 2000

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J. Chem. Soc., Perkin Trans. 1, 2000, 1037-1043

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Heterocalixarenes Part 3: Bis-oxo-bridged calix[1]cyclicurea[3]arene and calix[1]cyclicurea[1]pyridine[2]arenes. Synthesis, X-ray crystal structure and conformational analysis

S. Kumar, D. Paul, G. Hundal, M. S. Hundal and H. Singh, J. Chem. Soc., Perkin Trans. 1, 2000, 1037 DOI: 10.1039/A906883J

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Journal of the Chemical Society, Perkin Transactions 1