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1.2.1.3.5.4 Bucherer–Bergs Hydantoin Synthesis

DOI: 10.1055/sos-SD-210-00029

Ayaz, M.; De Moliner, F.; Morales, G. A.; Hulme, C.Science of Synthesis: Multicomponent Reactions, (20141118.

The hydantoin (imidazolidine-2,4-dione) scaffold is a common feature in bioactive entities and natural products.[‌102‌] It is thus unsurprising that a number of methods exist for its preparation.[‌102‌] Among the various strategies available, the long-established Bucherer–Bergs synthesis[‌94‌] is the most direct one due to its simplicity and effectiveness. Simple mixing of a ketone with potassium cyanide and ammonium carbonate affords chemotype 23 through what can be considered a Strecker variation incorporating an additional carbon dioxide molecule. The main limitation of the Bucherer–Bergs synthesis, however, is the presence of a single diversity point, namely the one brought by the carbonyl component. Typical examples dealing with cyclic ketones are shown in Scheme 22.[‌103‌]

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