Trimesic acid is a suitable building block in triple four-component Ugi reaction: access to unique trivalent compounds

Monatshefte für Chemie - Chemical Monthly - A triple four-component Ugi reaction of isocyanide, amine, aldehyde, and trimesic acid as the acid component with three acidic functional groups in...     

An unexpected coupling reaction between isocyanides and carboxylic acids: a method for the synthesis of highly stable symmetrical and unsymmetrical alkylamidine and arylamidine carbocations

An unexpected coupling reaction between isocyanides and carboxylic acids which led to the synthesis of highly stable symmetrical and unsymmetrical alkylamidine and arylamidine carbocations under mild reaction conditions is described. The structures of these compounds were confirmed by IR, mass, ¹H NMR, ¹³C NMR, and single-crystal X-ray diffraction studies and a plausible mechanism is proposed.     

Recent progress of isocyanide-based multicomponent reactions in Iran

The aim of this review is to provide an overview of the contributions and recent advances made by Iranian scientists in the field of isocyanide-based reactions between 1999 and 2009. With over 100 publications during this period, Iranians are responsible for approximately 10% of all publications in the world involving isocyanide-based multicomponent reactions (IMCRs). Some important aspects of these IMCRs include the execution of reactions in green reaction mediums like water or ethanol, high atom economies, mild reaction conditions, high yields, and catalyst-free processes. On the other hand, in most of these reactions, new classes of heterocyclic compounds with potential biological and medicinal activities have been reported.     

Meldrum's acid catalyzed reaction of tetracyanoethylene and aldehydes in water: a novel approach to arylidenemalononitrile

Meldrum's acid catalyzed the reaction of tetracyanoethylene with aromatic, heteroaromatic, and conjugated aldehydes led to arylidenemalononitrile in water in good yields at 80 degrees C. The work-up of reactions is very simple and the crude products are sufficiently pure to be used without further purification. The procedure provides an alternative method for the synthesis of arylidenemalononitrile.     

Asymmetric Reduction of Ketones with Catecholborane Using 2,6-BODOL Complexes of Titanium(IV) as Catalysts

Reductions performed with Ti^IV complexes of ligands based on bicyclo[2.2.2]octane diols 5 and 6 are effective catalysts in the reduction of prochiral ketones to optically active alcohols, with catecholborane as the reducing agent. Methyl ketones are favored and enantiomeric excesses (ee) of ≤98 % have been achieved with acetophenone as the substrate. Several other substrates were tested, among them 2-octanone, which gave 2-octanol in 87 % ee. Further details of the method were examined, for example, temperature, solvent composition, amount of molecular sieves (4 Å), and catecholborane quality, as well as the sensitivity of the ligands towards acids. NMR spectroscopic methods were used to gain some insight into the complexes formed between the ligands and [Ti(OiPr)₄]. A dimeric structure is proposed for the pre-catalyst.     

A mild and efficient approach for the selective deprotection of benzyl and phenyl trimethylsilyl ethers in 1-butyl-3-methyl-imidazolium chloride

1-Butyl-3-methyl-imidazolium chloride ([bmim]Cl) in the absence of any catalyst mediated the selective deprotection of benzyl and phenyl trimethylsilyl (TMS) ethers to the corresponding alcohols and phenol in good yields at room temperature even in presence of alkyl silyl ethers. The work-up of reactions is very simple and the products do not require further purification. The ionic liquid (IL) can be recycled and reused for several runs without any significant loss of activity.     

Synthesis of bis(1,5-disubstituted tetrazoles) via double four component Azido-Ugi reaction

A double four component Azido-Ugi reaction of isocyanide, TMSN₃, aldehyde, and 4,4′-sulfonyldianiline with two amine functional groups in MeOH at 65°C has been described. The synthesis of pharmacologically and structurally interesting compounds with two 1,5-disubstituted tetrazole rings via a reaction from available and inexpensive reagents under a convenient process and mild reaction conditions has been reported. Modifications in the structure of the reaction product could be followed by varying the aldehyde or isocyanide component. The products are new and were well described by Mass, ¹H NMR, and ¹³C NMR spectral studies.     

Synthesis of fully substituted pyrano[2,3-c]pyrazole derivatives via a multicomponent reaction of isocyanides

The three-component reaction of the zwitterions generated from dialkyl acetylenedicarboxylate and isocyanides with 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one is described. The reaction afforded the corresponding special type of fully substituted pyrano[2,3-c]pyrazole derivatives in good yields without using any catalyst and activation.     

Isocyanide‐Catalyzed Reaction of Tetracyanoethylene and Activated 1,3‐Dicarbonyl CH‐Acid Compounds: A Rapid and Efficient Synthesis of Pyran Annulated Heterocyclic Systems

An isocyanide‐catalyzed reaction between tetracyanoethylene and various activated CH‐acid compounds to afford the corresponding pyran annulated heterocyclic ring systems, in high yield at room temperature within a few minutes, is described. To the best of our knowledge, this is the first example in which isocyanide functions as only a catalyst but not a reagent.