Synthesis and reactivity of 5-methylenehydantoins

Poly(ethylene) glycols and mechanochemistry for the preparation of bioactive 3,5-disubstituted hydantoins

“…Various methodologies have been applied to the synthesis of 3,5-disubstituted hydantoins. A straightforward pathway is the alkylation/arylation [6][7][8][9][10] of the N-3 position of 5-or 5,5 0 -disubstituted hydantoins but most of the procedures describe the cyclisation of ureido derivatives of amino esters A, prepared by reaction with isocyanates (either in solution [11][12][13][14][15][16][17] or on solidsupport [18][19][20][21][22][23] ) (Method A, Scheme 1), phosgene, 24 or triphosgene. [25][26][27][28][29] We have recently demonstrated that mechanochemistry was successfully applied to the eco-friendly preparation of 5,5 0disubstituted hydantoins, 30 including the antiepileptic drug phenytoin (Phenytek®, Fig.…”

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

“…Therefore, it is considered to be a suitable position for basecatalyzed Knoevenagel condensation reactions with aldehydes to form 5-alkylidene hydantoins (15) (Scheme 1). 28 This product can also be prepared by Wittig-type reactions which use 5-phosphorylated Hydantoins (16) (Scheme 1). The introduction of an arylmethylene group at C-5 enhances the acidity of the N-1 hydrogen, making it quantifiable.…”

“…This results in the formation of organometallic complexes (Figure 3), and so hydantoin can adopt mono or bidentate behavior. [43][44] Some of these complexes (27,28) were tested and found to be strong cytotoxic agents.…”

An Efficient Route to Novel Uracil-Based Drug-Like Molecules

“…A similar procedure 21 was employed for the synthesis of the hydantoin derivative 5n and the 1-[3-(3,5-dichlorobenzoyl)benzyl]uracil 5m (Scheme 5). The benzyloxymethyl (BOM) protecting group was subsequently cleaved in a facile manner upon reflux in a mixture of hydrochloric acid and ethanol.…”