Domino condensation/aza-Michael/O→ N acyl migration of carbodiimides with activated α, β-unsaturated carboxylic acids to form hydantoins
A Volonterio, M Zanda
Index: Volonterio, Alessandro; Zanda, Matteo Tetrahedron Letters, 2003 , vol. 44, # 47 p. 8549 - 8551
Full Text: HTML
Citation Number: 33
Abstract
Activated α, β-unsaturated carboxylic acids undergo an unexpected domino condensation/aza-Michael/O→ N acyl migration with carbodiimides, producing N, N- disubstituted hydantoins in good yields. An array of structurally varied aspartic acid-derived hydantoins, including some fluorinated derivatives, have been synthesized by this method, whose scope and limits are discussed.
Related Articles:
A ribozyme with michaelase activity: synthesis of the substrate precursors
[Eisenfuehr, Alexander; Arora, Paramjit S; Sengle, Gerhard; Takaoka, Leo R; Nowick, James S; Famulok, Michael Bioorganic and medicinal chemistry, 2003 , vol. 11, # 2 p. 235 - 249]
Regioselective hydrolysis of diesters of (Z)-and (E)-2-methyl-butenedioic acids by PLE
[Schmid, Rudolf; Partali, Vassilia; Anthonsen, Thorleif; Anthonsen, Henrik W; Kvittingen, Lise Tetrahedron Letters, 2001 , vol. 42, # 48 p. 8543 - 8545]
Dynamics of theory change in chemistry: Part 1. The benzene problem 1865–1945
[Anschuetz Justus Liebigs Annalen der Chemie, 1907 , vol. 353, p. 144,178]