In the completion of our fluorine scan of tricyclic inhibitors to map the fluorophilicity/fluorophobicity of the thrombin active site, a series of 11 new ligands featuring alkyl, alkenyl, and fluoroalkyl groups was prepared to explore fluorine effects on binding into the hydrophobic proximal (P) pocket, lined by Tyr 60A and Trp 60D, His 57, and Leu 99. The synthesis of the tricyclic scaffolds w...

Recently, we have reported convenient methods for the synthesis of five-membered heterocycles by the use of 1,3-dipolar cycloaddition reactions.1,2) The introduction of chirality into the resulting cycloadducts was required for further application of these methods. Asymmetric synthesis or optical resolution by the use of enzymes is an effective method for obtaining chiral synthons, and pig live...

Highly soluble dimedone-derived o-alkoxyphenyliodonium ylides have been prepared and characterized by single crystal X-ray diffraction. These new iodonium ylides are useful reagents for the preparation of oxazole derivatives by reaction with carbodiimides.

Few-layer graphenes (FLG) produced by dispersion and exfoliation of graphite in N-methylpyrrolidone were successfully functionalized using the 1,3-dipolar cycloaddition of azomethine ylides. The amino functional groups attached to graphene sheets were quantified by the Kaiser test. These amino groups selectively bind to gold nanorods, which were introduced as contrast markers for the identifica...

The bond dissociation enthalpies (BDEs) of sulfur and selenium ylides have been estimated by applying MP2/6-311++G(3df,2p)//MP2/6-31G(d,p), G3, and other computational methods. Computed sulfoxide bond enthalpies were compared to experimental results to ensure the reliability of the computational methods before extending to related compounds. The examined ylides include the following: sulfoxides...

The Stevens and Sommelet–Hauser rearrangement of ammonium ylides are known as useful transformations for organic synthesis because they convert a readily accessible C–N bond into a new C–C bond. The Stevens rearrangement has been widely used for the asymmetric synthesis of α-amino acid derivatives, whereas the Sommelet–Hauser rearrangement is much less common because the Sommelet–Hauser rearran...

In a sustained search for novel ?-amylase inhibitors the treatment of type 2 diabetes mellitus (T2DM), we report herein synthesis series nineteen rhodanine-fused spiro[pyrrolidine-2,3?-oxindoles]. They were obtained by one-pot three component [3 + 2] cycloaddition stabilized azomethine ylides, generated in situ condensation glycine methyl ester and cyclic ketones 1H-indole-2,3-dione (isatin), w...