Cyanoacetylenes as Triggers and Partners in KOH-Assisted Assemblies of Quinoline-Based Dihydropyrimido[1,2-]quinolin-3-ones on Water.

Arylcyanoacetylenes trigger the assembly of dihydropyrimido[1,2-]quinolin-3-ones in good to excellent yields on the platform of quinolines in the presence of KOH in aqueous media at room temperature. This green on-water methodology provides a simple one-pot access to a novel family of the pharmaceutically prospective compounds.

Study of spontaneous E/Z isomerization of bis[(Z)-cyanomethylidene]-diazapentacyclodienedicarboxylates by H, C, and N NMR spectroscopy, X-ray, and quantum chemical calculation data.

X-ray data show that the diethyl 6,13-bis[(Z)-cyanomethylidene]-5,5,14,14-tetramethyl-4,15-dioxa-7,12-diazapentacyclo[9.5.2.

A domino reaction of alpha,beta-acetylenic gamma-hydroxy nitriles with arenecarboxylic acids: an unexpected facile shortcut to 4-cyano-3(2H)-furanones.

An unexpected facile domino reaction of alpha,beta-acetylenic gamma-hydroxy nitriles with arenecarboxylic acids (Et(3)N, MeCN, 20-25 degrees C, 48 h) affords 4-cyano-3(2H)-furanones in 67-86% yield. The reaction is triggered by the addition of an arenecarboxylic acid to a triple bond, followed by the domino reaction sequence: intramolecular transesterification-enol formation and Claisen condensation of the ketoacetonitrile tautomer with ester functional group.

Stereoselective C(2)-vinylation of 1-substituted imidazoles with 3-phenyl-2-propynenitrile.

First examples of direct vinylation of 1-substituted imidazoles at the 2-position of the imidazole nucleus are described. 1-Substituted imidazoles 1a-e are C(2)-vinylated with 3-phenyl-2-propynenitrile (2) at room temperature without catalyst and solvent to afford 3-(1-organyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitriles 3a-e, mainly (c.a.

Stereochemical study of iminodihydrofurans based on experimental measurements and SOPPA calculations of (13)C-(13)C spin-spin coupling constants.

Configurational assignment and conformational analysis of a series of iminodihydrofurans obtained from cyanoacetylenic alcohols were performed on the basis of experimental measurements and high-level ab initio calculations of their (13)C-(13)C spin-spin coupling constants. The title compounds were shown to form and exist in solution as the individual Z isomers, adopting the orthogonal orientation of the amino, alkylamino and dialkylamino groups and the s-trans orientation of the CONH(2) group at the C(4) position of the 2,5-dihydro-2-iminofuran moiety.