Oxidation with DMF/HIO4: A Convenient Preparation of Juglone

As part of an ongoing program directed toward the preparation of antraciclinones¹ and aryl substituted lapachones², which are important anticancer and antibiotic³ agents, we became interested in a efficient synthesis of substituted 1,4-naphthoquinones, such as juglone (3). This compound has received some attention due its activity as an allelophatic compound⁴. An extensive analysis of the literature procedures indicated that several methods are available starting from 1,5-dihydroxynaphthalene (1). All the procedures explored the oxidation of carbon four of the naphthyl ring by several known reagents, such as, chromium trioxide-piridine⁵, thallium trinitrate⁵, chromic acid⁶, peracetic acid⁷, dichromate⁸, iron (III) chloride⁹ and mercuric oxide¹⁰. None of the several known methods for the preparation of (3) proceeded in satisfactory yield (except for the thallium trinitrate method which gave 642 yield) and most of them gave a mixture of 1,2 and 1,4-naphthoquinone.     

Thermal degradation mechanism for citalopram and escitalopram

Journal of Thermal Analysis and Calorimetry - Citalopram, [(R,S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile] hydrobromide and its S-isomer, escitalopram...     

Indecomposable involutive set-theoretic solutions of the Yang–Baxter equation

We describe the indecomposable involutive non-degenerate set-theoretic solutions of the Yang–Baxter equation as dynamical extensions of non-degenerate left cycle sets. Moreover we characterize the indecomposable dynamical extensions and we produce several examples. As an application we construct a family of finite indecomposable solutions whose structure groups have not the unique product property.     

Hexanes/acetonitrile: a binary solvent system for the efficient monosilylation of symmetric primary and secondary diols

Symmetric diols are useful compounds in the synthesis of natural products, their value often dependent on their successful monoprotection. A general and simple method for the monosilylation of symmetrical primary and secondary diols is reported. The method exploits the solubility differential of diols and their monosilylated counterparts in a binary hexanes/acetonitrile solvent system.     

UV filter 2‐ethylhexyl 4‐methoxycinnamate: a structure,energetic and UV–vis spectral analysis based on density functional theory

2‐Ethylhexyl 4‐methoxycinnamate (EHMC) is a very commonly used UVB filter that is known to isomerize from the (E) to the (Z) isomer in the presence of light. In this study, we have performed high level quantum chemical calculations using density functional theory (DFT) with the B3LYP density functional and extended basis sets to study the gas‐phase molecular structure of EHMC and its energetic stability. Calculations were also performed for related smaller molecules cinnamic acid and 4‐methoxycinnamic acid. Charge delocalization has been analyzed using natural charges and Wiberg bond indexes within the natural bond orbital analysis and using nucleus independent chemical shifts. Density functional theory calculations reveal that the (E) isomer of EHMC is more stable than the (Z) by about 20 kJ mol^?1 in both the gas and aqueous phases. The enthalpy of formation in the gas phase of (E)‐EHMC was derived from an isodesmic bond separation reaction. Long‐range corrected DFT calculations in implicit water were made in order to understand the excited state properties of the (E) and (Z) isomers of EHMC. Copyright © 2013 John Wiley & Sons, Ltd.