40856-87-9

Usage

InChI:InChI=1/C6H8N2O2/c9-5-4-2-1-3-8(4)6(10)7-5/h4H,1-3H2,(H,7,9,10)/t4-/m0/s1

Upstream product

• 590-28-3 potassium cyanate 
• 147-85-3 L-proline 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 38605-65-1 (S)-1-[¹³C]carbamoylpyrrolidine-2-carboxylic acid 

Downstream Products

• 122481-21-4 (-)-(S)-tetrahydro-1H-pyrrolo[1,2-c]imidazol-3(2H)-one 

Relevant academic research and scientific papers

Cu-catalyzed C(sp2)-N-bond coupling of boronic acids and cyclic imides

A general Cu-catalyzed strategy for coupling cyclic imides and alkenylboronic acids by forming C(sp2)-N-bonds is reported. The method enables the practical and mild preparation of (E)-enimides. A large range of cyclic imides are allowed, and di- and tri-substituted alkenylboronic acids can be used. Full retention was observed in the configuration of the alkene double bond in the coupled products. The method is also applicable for preparing N-arylimides, using arylboronic acids as coupling partners. The usefulness of this strategy is exemplified by the convenient derivatization of the chemotherapy medication 5-flurouracil, the nucleoside uridine and the anti-epileptic drug phenytoin.

Cu-catalyzed N-3-Arylation of Hydantoins Using Diaryliodonium Salts

A general Cu-catalyzed, regioselective method for the N-3-arylation of hydantoins is described. The protocol utilizes aryl(trimethoxyphenyl)iodonium tosylate as the arylating agent in the presence of triethylamine and a catalytic amount of a simple Cu-salt. The method is compatible with structurally diverse hydantoins and operates well with neutral aryl groups or aryl groups bearing weakly donating/withdrawing elements. It is also applicable for the rapid diversification of pharmaceutically relevant hydantoins.

Revisiting the Urech Synthesis of Hydantoins: Direct Access to Enantiopure 1,5-Substituted Hydantoins Using Cyanobenziodoxolone

A method for the synthesis of enantiopure 1,5-substituted hydantoins was developed using a hypervalent iodine cyanation reagent (cyanobenziodoxolone, CBX) as a source of electrophilic carbon. Starting from inexpensive commercially available enantiopure protected amino acids, the method allowed the synthesis of various hydantoins without epimerization. Formation of hydantoins from dipeptides was also possible, but partial epimerization was observed in this case. This synthetic strategy is user friendly as CBX is a bench-stable easy-to-handle crystalline reagent and avoids conventional multistep protocols, thus allowing the facile synthesis of a library of chiral hydantoins.

Mechanochemical preparation of hydantoins from amino esters: Application to the synthesis of the antiepileptic drug phenytoin

The eco-friendly preparation of 5- and 5,5-disubstituted hydantoins from various amino ester hydrochlorides and potassium cyanate in a planetary ball-mill is described. The one-pot/two-step protocol consisted in the formation of ureido ester intermediates, followed by a base-catalyzed cyclization to hydantoins. This easy-handling mechanochemical methodology was applied to a large variety of α- and β-amino esters, in smooth conditions, leading to hydantoins in good yields and with no need of purification steps. As an example, the methodology was applied to the "green" synthesis of the antiepileptic drug Phenytoin, with no use of any harmful organic solvent.

Synthesis and crystal structure determination of hydantoin-l-proline

The title compound, hydantoin-l-proline, C6H8N 2O2, crystallize in the orthorhombic system with space group P212121 (N°19), Z = 4, and unit cell parameters a = 7.136(1) A, b = 8.009(2) A, c = 11.378(2) A. The molecular structure shows a hydantoin and pyrrolidine ring coupling forming a bicyclohydantoin. The crystal packing is governed by N-H???O hydrogen bond-type intermolecular interactions, forming infinite one-dimensional chains.