The structure and configuration of the series of previously unknown arylaminomethylidenefuran-2(3H)-ones have been determined in solution by H, C, N nuclear magnetic resonance spectroscopy including two-dimensional experiments such as H─ H COSY, dqCOSY, H─ C HSQC, H─ C HMBC. It was found that synthesized substances exist as an equilibrium mixture of E- and Z-enamines in solution. It was established on the basis of density functional theory calculations that the exchange between the two push-pull enamines is a simple rotation around an exocyclic partial double bond that depends on the effect of the solvents. Copyright © 2017 John Wiley & Sons, Ltd.

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UDC 547.724The X-ray crystallographic method is used to determine the crystal structure and characteristic features of the molecular structure of 3-(2-(2-nitrophenyl)hydrazono)-5-phenyl-3H-furan-2-one produced by the reaction of azo coupling of 2-nitrophenyldiazonium salt with 5-phenyl-3Н-furan-2-one.

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Previously unknown dispiropyrrolidines were synthesized by 1,3-dipolar cycloaddition of azomethine ylide to 3-arylmethylidene-3Н-furan-2-ones. The cycloaddition reaction was demonstrated to proceed diastereoselectively through an endo-transition state. Alternative transition states for the reaction are discussed.

In the crystal structure of the title compound, C 23 H 19 N 5 O 3 Á0.58C 2 H 6 OSÁ-0.42C 2 H 3 N, prepared by the azo coupling of the 4-nitrophenyldiazonium salt with 3a-(p-tolyl)-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-1-one, the azo molecules are linked by N-HÁ Á ÁO hydrogen bonds into chains along the a-axis direction, and by the -interaction into [101] chains. The dimethyl sulfoxide and acetonitrile solvent molecules occupy the same positions, with populations of 0.585 (3) and 0.415 (3), respectively. These molecules take part in C-HÁ Á ÁO(N) and C-HÁ Á Á contacts. The energy of the -interactions was estimated using DFT calculations. The Hirshfeld molecular surface analysis revealed the positions of the most important intermolecular contacts, such as hydrogen bonds and -interactions.