P-Toluenesulfonylmethyl isocyanide

The use of a vinylphosphonium salt as the source of the QQ fragment instead of the more commonly employed 1,2-dicarbonyl substrate is illustrated by the pyrrole synthesis in Scheme 79b (8UOC2570). A particularly interesting feature is the intramolecular Wittig reaction with an amide carbonyl group. A very useful synthesis of pyrroles depends upon the addition of the anion of p-toluenesulfonylmethyl isocyanide (TOSMIC) to a,/3-unsatur-... 

A useful pyrrole synthesis depends upon the addition of the anion of p-toluenesulfonylmethyl isocyanide (TOSMIC) to a,(3-unsaturated ketones or other Michael acceptors (72TL5337) (Scheme 56). 

Samanta et al. [23] conveniently synthesized the 1,5-disubstituted imidazoles (xxv) on a polymeric support using base-promoted 1,3-dipolar cycloaddition reaction of p-toluenesulfonylmethyl isocyanide (TOSMIC) with immobilized imines under microwave irradiation. 

Samanta SK, Kylanlahti 1, Yli-Kauhaluoma J (2005) Microwave-assisted synthesis of imidazoles reaction of p-toluenesulfonylmethyl isocyanide and polymer-bound imines. Bioorg Med Chem Lett 15 3717-3719... 

PS-p-toluenesulfonylmethyl isocyanide (TosMIC) reagent, developed by Barrett et al. was found to be effective for the conversion of a range of aryl aldehydes into highly pure 4-aryl oxazoles in the presence of BTMG (2) [79] (Scheme 4.29b). A typical procedure involved the reaction of aldehyde with the gel (4 equiv.) in acetonitrile (0.2M sol) and BTMG (2) (4 equiv.) for 12 h at 65 °C. ... 

Diethoxyphosphoryl-4-methyl-3-phenyl B. From p-toluenesulfonylmethyl isocyanide (TsMIC) 2-Nitropropen-1 -ylbenzene 58 93S473... 

A new silver-catalyzed heteroaromatization of propargyhc alcohols with p-toluenesulfonylmethyl isocyanide (TosMIC) was developed that provided an efficient and modular approach to sulfonyl benzo[l ]furans.The TosMIC played a dual role sulfonyl source and ligand (14OL6204). 

The reaction of solid-supported imines and p-toluenesulfonylmethyl isocyanide (TOSMIC) gave resin-bound imidazoles. In this case, the cleavage of the products occurred with the 2-methoxy-substituted linker because the imidazole core was attached directly to the aryl ring with a carbon-carbon bond. 

Diverse sugar-derived aldehydes 15 (Scheme 11.6) were used as chiral auxiliaries to perform the diastereoselective three-component Passerini reaction by reaction with p-toluenesulfonylmethyl isocyanide (17a, TosMIC) and carboxylic acids 16, giving... 

Krishna, P. R., Dayaker, G., Reddy, P. V. N. (2006). Diastereoselective Passerini reaction using p-toluenesulfonylmethyl isocyanide (TosMIC) as the isonitrile component. Tetrahedron Letters, 47, 5977-5980. 

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