New, Diastereoselective One-Pot Synthesis of Tetrasubstituted Hydantoins

✍ Scribed by Abdolali Alizadeh; Hassan Masrouri

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: German
• Weight: 91 KB
• Volume: 89
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200690117

✦ Synopsis

Abstract

An effective route to hydantoins is described, based on the 2 : 1 : 1 addition of arylsulfonyl isocyanates, dialkyl acetylenedicarboxylates, and dialkyl trialkylsilyl phosphites. The resulting tetrasubstituted, stable hydantoins 4/4′ (Table) were obtained in excellent yields, and their structures were corroborated spectroscopically (IR, ^1^H‐, ^13^C‐, ^31^P‐NMR, EI‐MS) and by elemental analyses. A plausible mechanism for this type of cyclization is proposed (Scheme 2).