A series of conjugated donor−acceptor trienes in which the central double bond is incorporated into an unsaturated isophorone, verbenone, or chromone ring has been synthesized. In each case, the donor group consists of an amine and an aromatic or heterocyclic ring system, and the acceptor is the dicyanomethylidene group. The nonlinear optical properties of each of the compounds has been measured and correlated with its structure. The dipole moments and molecular hyperpolarizabilities of these compounds, like those of other conjugated polyenes, are large enough to be used as the active components of electrooptic polymers. Unlike other donor−acceptor polyenes, however, these compounds exhibit the thermal stability required for such applications.

Synthesis and Nonlinearity of Triene Chromophores Containing the Cyclohexene Ring Structure

In 2-Stellung unsubstituierte 3-Acyl-chromone wurden aus 2-Hydroxy-ω-acyl-acetophenonen durch Reaktion mit Orthoameisensaure-triathylester und Acetanhydrid oder aus 2-Hydroxy-ω-formyl-acetophenon und Acetanhydrid/Natriumacetat dargestellt. Strukturbeweise wurden mit Hilfe von UV-, IR- und NMR-Spektren gefuhrt.

3‐Acylchromone. XV. Mitt. über Untersuchungen an γ‐Pyronen

o-Hydroxy-ω-formyl-acetophenon (2a) reagiert mit Aldehyden zu aryl- bzw. alkyl-substituierten Chromonyl-(3)-carbinolen (6, 11–14) oder Bis-chromonyl-methan-Derivaten (20, 21). Verbindungen des Typs 6 bzw. 14 konnen zu 3-Acyl-chromonen (3a, b) oxydiert werden.

Untersuchungen an γ‐Pyronen, XIV. Über die Reaktion von o‐Hydroxy‐ω‐formyl‐acetophenon mit Aldehyden

An efficient method for synthesis of 1,3-dimethyl-5-(2-phenyl-4H-chromen-4-ylidene)pyrimidine-2,4,6(1H,3H,5H)-triones has been developed by treatment of 2-hydroxychalcones and 1,3-dimethylbarbituric acid in refluxing toluene in the presence of amberlyst-15 as catalyst in air. The process involves the occurrence of a domino sequence of Michael addition, cyclization and aerial oxidation. The compounds synthesized showed an interesting property of free rotation around the bond linking the two heterocyclic moieties and three of them were found to show binding property with the milk protein β-lactoglobulin (β-lg). DFT and docking (with β-lg) studies of one of the compounds have been done.

An efficient synthesis of 1,3-dimethyl-5-(2-phenyl-4H-chromen-4-ylidene) pyrimidine-2,4,6(1H,3H,5H)-triones and investigation of their interactions with β-lactoglobiulin

3-Benzoyl-chromon (1) setzt sich mit 1.3-Dimethyl-barbitursaure (4), je nach Reaktionsbedingungen, zu den 3-substituierten Flavon-Derivaten 5 bzw. 9 um.

I. Kochs

Papers

[Contribution on the analysis of benze-4-pyrones. 13. Report on the studies of gamma-pyrones]