One-pot synthesis of functionalized hydantoin derivatives via a four-component reaction between an amine, an arylsulfonyl isocyanate and an alkyl propiolate or dialkyl acetylenedicarboxylate in the presence of triphenylphosphine

Acyclic and Cyclic Ureas (Update 2013)

“…[259] Interestingly, whereas formation of the Z-configured products is observed in the presence of isoquinoline, E-configured products result when triphenylphosphine is used instead. [260] Similar hydantoin derivatives are prepared from aryl isocyanates and alkyl propynoates in the presence of potassium thiocyanate. [261] Other variations of this approach involve reaction between dialkyl trialkylsilyl phosphites, arylsulfonyl isocyanates, and dialkyl acetylenedicarboxylates to give the phosphonic acid esters 52 [262] or trialkyl phosphites, arylsulfonyl isocyanates, and dialkyl acetylenedicarboxylates to give the phosphorous ylides 53 (Scheme 96).…”

Utility of Acetylenedicarboxylate in Organic Synthesis

“…Alizadeh and Sheikhi are reported the preparation of methyl 2‐[1‐substituted‐2,5‐dioxo‐3‐(substituted sulfon‐yl)tetrahydro‐4 H ‐imidazol‐4‐yieldne]acetates 113a , 113b , 113c via simple one‐pot reactions between primary amines 112a , 112b , DMAD ( 1a ) and arylsulfonyl isocyanates 78a , 78b in dichloromethane at room temperature in the presence of triphenylphosphine (Scheme ) .…”

“…N , N ‐Disubstituted thioureas 160a , 160b reacted with DMAD ( 1a ) to give thiazolidinones 161a , 161b . The structure of thiazolidinones 161b was proved by 13 C‐NMR spectroscopy and X‐ray analysis (Scheme ).…”

Solvent-free highly regioselective Michael addition of phenytoin to α,β-unsaturated esters in the presence of TBAB under ultrasound irradiation

“…This heterocycle is a useful pharmacological compound and extensively used as an anticonvulsant agent, 7 treatment of epileptic seizures, 8,9 epidermolysis bullosa, 10 inflammatory conditions, case of anticonvulsant activity of DPH, it has been established that the site of the action of this compound is the neuronal voltage-sensitive sodium channel, though no more information about the location and nature of this site has been reported. 14,15 In contrast to the many examples of the Michael addition amines on different unsaturated systems, there are only a few reports on the amides and imides Michael reaction (due to the low reactivity of them) with these systems. [16][17][18][19] Although, neutral amides and imides have very restricted nucleophilicity, but in the presence of a convenient base, nitrogen anions derived from them can become more satisfactory nucleophiles in Michael-type reactions.…”