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12.3.1.5.1.9 Method 9: Reaction of the Enolate of Ethyl Isocyanoacetate with an Isothiourea

DOI: 10.1055/sos-SD-012-00398

Grimmett, M. R.Science of Synthesis, (200212402.

This type of process is analogous to tosylmethyl isocyanide cyclocondensations. The enolate of ethyl isocyanoacetate 169 reacts with an isothiourea to give 170 and/or 171 (alkyl 5-aminoimidazole-4-carboxylates) (Scheme 86).[‌302‌] As such, the method provides a short, mild alternative to the multistep cyclization of α-formamido-substituted amidines,[‌303‌] or the condensation of an α-(ethoxymethyleneamino)cyanoacetate[‌258‌] (Section 12.3.1.6.1). Control of regiochemistry is a problem with unsymmetrical isothioureas.

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