Calixarenes and related compounds are established scaffolds useful as ligands and very popular as building blocks for molecular design. At the same time, the use of these compounds is virtually always defined by the ability of researchers to prepare them efficiently in useful quantities, and in a controlled fashion. As an example, calix[4]arenes, calix[6]arenes, and calix[8]arenes gained popula...

In this report, we describe a new method for the synthesis of densely functionalized 2(1H)-pyrazinones. Treatment of mesoionic 1,3-oxazolium-5-olates with carbanions derived from activated methylene isocyanides (p-toluenesulfonylmethyl isocyanide (TosMIC) and ethyl isocyanoacetate) causes a novel ring transformation affording 2(1H)-pyrazinones in moderate to high yields. The cytotoxicity and an...

We introduce a four component Passerini polymerization utilizing sterically bulky isocyanide monomers.

A facile synthesis of highly functionalized 2H-iminopyran derivatives by the multi-component reaction of cyclohexyl isocyanide, dialkyl acetylenedicarboxylates, arylglyoxals and arylamines is described. The zwitterionic intermediate produced by addition of cyclohexyl isocyanide to electron-deficient acetylene diesters was trapped by the electrophilic imine moiety of α-iminoketones, derived from...

New melanin synthesis inhibitors, melanocins A, B and C, were isolated from the fermentation broth and mycelium extract of Eupenicillium shearii F80695. Melanocin A, an isocyanide compound, inhibited mushroom tyrosinase and melanin biosynthesis of B16 melanoma cells with IC50 value of 9.0 nM and MIC value of 0.9 microM, respectively. Melanocin A also inhibited growth of Streptomyces bikiniensis...

An alternative approach toward the simple and robust synthesis of highly substituted peptidic thiazole derivatives using Ugi-multicomponent reaction (U-MCR) is described. Thus, we introduced the enantiopure (R)-2-methyl-2-isocyano-3-(tritylthio)propanoate as a novel class of isocyanide in MCR. This bifunctional isocyanide was found to undergo mild cyclodehydration to afford thiazole containing ...

We present strong detections of methyl cyanide (CH3CN), vinyl cyanide (CH2CHCN), ethyl cyanide (CH3CH2CN) and cyanodiacetylene (HC4CN) molecules with the Green Bank Telescope (GBT) toward the Sgr B2(N) molecular cloud. Attempts to detect the corresponding isocyanide isomers were only successful in the case of methyl isocyanide (CH3NC) for its JK = 10 − 00 transition, which is the first interste...

The complex [ { Rh(p-Pz)(CNBut)2)2] (1) acts as a supernucleophile due to the strong basicity induced by the isocyanide ligands. It reacts rapidly with halocarbons (RX) such as PhCH2Cl or Me1 to give the cationic dirhodium(II1) complexes of formula [ { Rh(p-Pz)(R)(CNBut)2)2(p-X)]X. These reactions are stereoselective since the single stereoisomer formed presents both organic groups ( P h C H 2 ...