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Preparation of 3-(10′-halo-9′-anthracenyl) isoxazolecarboxylic esters

✍ Scribed by Xiaochun Han; Brendan Twamley; Nicholas R. Natale

Publisher: Journal of Heterocyclic Chemistry
Year: 2003
Tongue: English
Weight: 114 KB
Volume: 40
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570400321

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✦ Synopsis

Abstract

The 10‐halo (Cl or Br) anthracene‐9‐nitrile oxides (1a,b) were obtained directly from the treatment of 9‐anthracenylaldoxime with N‐halosuccinimide (NCS or NBS) in DMF. The 3‐(10′‐halo‐9′‐anthracenyl)‐5‐isoxazolecarboxylic esters (5a,b and 6a,b) were prepared via 1,3‐dipolar cycloaddition between the obtained nitrile oxides 1a (or 1b) and two different dipolarophiles: ethyl β‐pyrrolidinocrotonate (an enamine of ethyl acetoacetate) or dimethyl acetylenedicarbox‐ylate (DMAD) respectively. The 10 (or 10′)‐ position of the anthracene in either anthracene‐9‐nitrile oxide or 3‐(9′‐anthracenyl) isoxazole molecules (3,4) is readily halogenated by N‐halosuc‐cinimide in DMF. X‐ray studies showed that 5a possesses two aromatic ring systems that lie at 74.4° from coplanarity. The bond linking the two ring systems is 1.4893(18) Å, indicating only partial conjugation between the two ring systems. The crystal lattice showed unique head‐to‐tail intermolecular stacking of anthracene rings.

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