Reaction between Dialkyl Acetylenedicarboxylates and Arylsulfonyl Isocyanates in the Presence of Trialkyl Phosphites: A Simple and Efficient Synthesis of Tetrasubstituted Hydantoins

Abstract

An effective route to novel hydantoins is described. This involves reaction of dialkyl acetylenedicarboxylates and arylsulfonyl isocyanates in the presence of trialkyl phosphites. Stable crystalline phosphorus ylides are obtained in excellent yields from the 1:1:2 addition reaction between trialkyl phosphites and dialkyl acetylenedicarboxylates in the presence of arylsulfonyl isocyanates. These hydantoin-containing phosphoranes exist in solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon-carbon double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group.

Key words

trialkyl phosphites - dialkyl acetylenedicarboxylates - arylsulfonyl isocyanates - multicomponent reaction - hydantoin

References

• 1 Randall FJ. Johnson AW. Tetrahedron Lett.  1968,  2841 
• 2 Zeliger HI. Snyder PJ. Tetrahedron Lett.  1969,  2199 
• 3 Snyder PJ. Tetrahedron Lett.  1971,  215 
• 4 Zbiral E. Synthesis  1974,  775 
• 5 Becker KB. Tetrahedron  1987,  36:  1717 
• 6 Ferrer P. Auendano C. Sollhuber M. Liebigs Ann. Chem.  1995,  1895 
• 7 Johnson AW. Ylid Chemistry   Academic Press; New York: 1966. 
• 8 Kolodiazhynyi OI. Russ. Chem. Rev.  1997,  66:  225 
• 9 Bestmann HJ. Vostrowsky O. Top. Curr. Chem.  1983,  109:  85 
• 10 Yavari I. Anary-Abbasinejad M. Alizadeh A. Tetrahedron Lett.  2002,  43:  4503 
• 11 Yavari I. Adib M. Tetrahedron  2001,  57:  5873 
• 12 Yavari I. Alizadeh A. Synthesis  2004,  237