P. Carroll, R. Mack, V. Georgiev
Feb 15, 1988
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Journal
Acta Crystallographica Section C-crystal Structure Communications
Abstract
C 18HI6N203, M r -" 308.34, monoclinic, C2/c, a = 19.482 (3), b = 7.642 (1), c = 21.695 (3)A, f l= 110.87 (1) °, V = 3018.1 (8) A 3, z = 8, D x = 1.357 gcm -3, 2(Mo Kct) = 0.71073 A, p = 0.88 cm -~, F(000)-1296, T = 297 K, final R = 0.045 for 1856 unique observed reflections. The title compound was derived from a 4,5-dihydro-4-oxo-2-(phenylamino)-3furancarboxylic acid via a novel 3(2H)-furanone2(5H)-furanone rearrangement. The amide and amine N atoms participate in the conjugated n system and the N--H's participate in intrarnolecular hydrogen bonding. Introducdon. Recently (Mack & Georgiev, 1987), we reported a novel 3(2H)-furanone-2(5H)-furanone rearrangement which was accomplished by treating 2-(N-substituted amino)-4,5-dihydro-4-oxo-3-furancarboxylic acids (1) with 1 equivalent of di(2-oxo-1,3-oxazolidin-3-yl)phosphinic chloride (2) and an appropriately substituted aromatic amine (3), in the presence of triethylamine. The rearrangement resulted * To whom all correspondence should be addressed. 0108-2701/88/020294-03503100 in the facile synthesis of a new class of 2(5H)-furanone amides (4). An X-ray crystal-structure determination of 2, 5-dihydro-4-I (4-methylphenyl)aminol-2-oxo-N-phenyl3-furancarboxamide (4a) was undertaken to define unambiguously the structures of 2(5H)-furanone