Benzotriazol-l-yl-methyl isocyanide

In the presence of Bu OK, (benzotriazole-l-yl)methyl isocyanide (BetMIC) 697 undergoes alkylation on the methylene group to give isocyanide 698. The anion derived from 698, upon its treatment with Bu OK, adds to the electron-deficient double bonds of ajl-unsaturated ketones, esters or nitriles to produce pyrroles 699. A similar reaction of isocyanide 698 with Schiff bases provides imidazoles 700. In both cases, use of unsubstituted isonitriles 697 in the reactions leads to heterocycles 699 and 700 with R1 = H (Scheme 108) <1997H(44)67>. 

Benzotriazole-l-yl)methyl isocyanide (BetMIC) 813 can be used instead of TosMIC in pyrrole syntheses thus, C-alkylation on the methylene group using /-BuOK and then reaction of the resulting give isocyanide 814 with, -unsaturated ketones, esters, or nitriles produces pyrroles 815 (Scheme 173) <1997H67>. 

Benzotriazol-l-yl-methyl Isocyanide The benzotriazol-l-yl-methyl isocyanide (BetMIC, Ij), first synthesized by Katritzky et al., is known as Katritzky s CIC [43]. It can be easily synthesized in two steps from commercially available benzotriazole (Bet, 93), paraformaldehyde (9c), and formamide (9h) to initially give... 

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