Recent developments in isocyanide based multicomponent reactions in applied chemistry

Multicomponent reactions (MCRs) are one-pot reactions employing more than two starting materials, e.g. 3, 4, … 7, where most of the atoms of the starting materials are incorporated in the final product.1 Several descriptive tags are regularly attached to MCRs (Fig. 1): they are atom economic, e.g. the majority if not all of the atoms of the starting materials are incorporated in the product; they are efficient, e.g. they efficiently yield the product since the product is formed in one-step instead of multiple sequential steps; they are convergent, e.g. several starting materials combine in one reaction to form the product; they exhibit a very high bond-forming-index (BFI), e.g. several non-hydrogen atom bonds are formed in one synthetic transformation.2 Therefore MCRs are often a useful alternative to sequential multistep synthesis.






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Figure 1


Above: multistep syntheses can be divergent (sequential) or convergent; below: in analogy MCR reactions are convergent and one or two component reactions are divergent or less convergent.

Chemistry and Biology Of Multicomponent Reactions

This Minireview highlights recent advances in the field of aryne and cyclohexyne chemistry that have allowed the extraordinary reactivity of these entities to be harnessed during the course of natural product syntheses. The syntheses presented rely on the use of these reactive species in chemoselective transformations and follow unprecedented synthetic strategies that are inspiring for the practitioners of synthetic organic chemistry.

Arynes and cyclohexyne in natural product synthesis.

Ketenimines are an important class of reactive species and useful synthetic intermediates. During the last two decades several practical and versatile approaches to ketenimines have been developed, leading to exhaustive investigations on ketenimine chemistry and the discovery of a variety of highly efficient reactions. Five types of reactions for ketenimines have been reported, including nucleophilic additions (ketenimines can be used as both electrophiles and nucleophiles), radical additions, cycloaddition reactions, electrocyclic ring closure reactions, and σ rearrangements. Furthermore, numerous complex organic compounds, particularly the biologically interesting heterocycles, have been constructed using these methodologies. The review of these accomplishments is presented here.

The thriving chemistry of ketenimines

Silver nanoparticles are particles in the size ranging between 1 and 100 nm. The two major methods used for synthesis of silver nanoparticle are the physical and chemical methods with the d...

Pharmaceutical aspects of silver nanoparticles

Reaction between alkyl isocyanides and dimethyl acetylenedicarboxylate in the presence of polyhydroxybenzenes. Synthesis of 4H-chromene derivatives

Characterization and the evaluation of antimicrobial activities of silver nanoparticles biosynthesized from Carya illinoinensis leaf extract

An effective route to novel coumarines and 4H-chromenes is described. This involves the reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-hydroxybenzaldehydes.

Synthesis of coumarines and 4H-chromenes through the reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in presence of 2-hydroxybenzaldehydes

Addition of catechol to methyl propiolate or ethyl phenylpropiolate in the presence of Ph 3 P leads to methyl 2-(1,3-benzodioxol-2-yl)acetate or 3-(1-phenylmethylidene)-1,4-benzodioxin-2-one. 2-Aminophenols react with alkyl propiolates in the presence of Ph 3 P to produce a nearly 1:1 mixture of 3-methyl-2H-1,4-benzoxazin-2-one derivatives and methyl (E)-3-(2-aminophenoxy)-2-propenoates.

Hoorieh Djahaniani

Papers

Reaction between alkyl isocyanides and dimethyl acetylenedicarboxylate in the presence of polyhydroxybenzenes. Synthesis of 4H-chromene derivatives

Characterization and the evaluation of antimicrobial activities of silver nanoparticles biosynthesized from Carya illinoinensis leaf extract

Synthesis of coumarines and 4H-chromenes through the reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in presence of 2-hydroxybenzaldehydes

Vinylphosphonium salt mediated reaction between alkyl propiolates and aminophenols or hydroxyphenols

One-step synthesis of substituted 4,7-bis[alkyl(aryl)imino]-3-oxa-6-thia-1-azaspiro[4.4]nona-1,8-dienes