Isocyanides reactions with

Ring closures which depend on the conversion of the heteroatom into an electrophile are mostly associated with the formation of thiophene, selenophene and tellurophene rings and some illustrative examples are shown in Scheme 17. The last example which concerns the conversion of electrophilic nitrogen species on the aryl ring. 

Erker and Trinkl synthesized the tricycles 177 as novel GABA-A/benzodiazepine receptor ligands via synthesis of enol phosphates such as 175 and reaction with isocyanides 176 (Scheme 13) <2001H1963>. 

In studying the reactivity of iV-fluoropyridinium fluoride 127 obtained from pyridine 126 by treatment with fluorine gas in chloroform at low temperature (Scheme 30), Kiselyov studied reactions with isocyanides in the presence of trimethylsilylazide <2005TL4851>. A mixture of products was obtained in which, besides tetrazolylpyr-idine 128 and a nicotinamide derivative 129 also tetrazolo[l,5-tf]pyridine 1 was obtained in very poor yield (5-10%). 

Tokitoh et al. have synthesized a sterically hindered disilene TbtMesSiSiMesTbt 210 that is kinetically stable but thermally labile, thus providing the corresponding silylene TbtMesSi 211, whose reaction with isocyanides bearing bulky substituents has resulted in the formation of the first stable silylene isocyanide complexes TbtMesSiCNR (212, R = Tbt 213, R = Mes ) (Scheme 30).327... 

Domling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed Engl 39 3169-3210... 

Domling, A. and Ugi, I., Multicomponent reactions with isocyanides, Angew. Chem., Int. Ed. Engl., 2000, 39, 3168-3210 Weber, L., Illgen, K. and Almsttetter, M., Discovery of new multi component reactions with combinatorial methods, Synlett, 1999, 3, 366-374. 

Domling, A. and Ugi, I., Multi-component reactions with isocyanides, Angew. Chem., Int. Ed. Engl, 2000, 39, 3169. 

A review of lone pair effects involving multiple bonds between heavier main group elements contains much of relevance to pj -bonded phosphorus systems. The diphosphene (295) has been shown to undergo cycloaddition reactions with isocyanides, to give the iminodiphosphiranes (296)." A thirtyfive-fold excess of methyl triflate is needed to convert the diphosphene (297) to the salt (298), which is unstable in non-polar solvents. Experimental data show that the P=P bond becomes stronger on alkylation as is the case for N=N compounds. 

With these species in hand, coordination polymers were prepared by reaction with isocyanides according to Eq. 7.35 42... 

Similar substitution reactions with isocyanides occur, which seldom proceed beyond disubstitution, even under drastic conditions" . 

---