2,4-Oxazolidinediones synthesis

Oxazolidine-4,5-dione, At-benzoyl-synthesis, 6, 231 Oxazolidinediones reactions, 6, 214 structure, 6, 179 Oxazolidine-2,4-diones as anticonvulsants, 1, 166 NMI 6, 181 reactions, 6, 214 s mthesis, 6, 231 OxazoIidine-2,5-diones crystal structure, 6, 185 reactions, 6, 214 polymers, 1, 307 s mthesis, 6, 231 Oxazolidine-4,5-diones synthesis, 6, 231 Oxazolidines... 

As Moody and co-workers (173) discovered, isomtinchnones can occasionally form even when they are not the desired product Thus, these workers inadvertently obtained an oxazolidinedione via an isomtinchnone rather than the desired oxoindo-line when a diazo compound was treated with rhodium(II) perfluorobutyramide in their studies leading ultimately to a synthesis of the marine alkaloid convolutamy-dine C. 

In principle then, these saturated imides and derivatives are beyond the scope of this chapter. However, the synthesis and reactions of some 3-unsubstituted derivatives of 179 are included in the interest of completeness. No attempt has been made to provide an exhaustive review of all examples of 2,4-oxazolidinediones. Rather, selected examples from the recent literature that illustrate general synthetic approaches or novel reactions are described. 

Further refinements in the reaction conditions resulted in a general synthesis of 3,5-dialkyl- and 3,5,5-trialkyl-2,4-oxazolidinediones including trimethadione... 

Oxazolidinediones are important in peptide synthesis (see Section 4.18.3.2.2(iii)) several methods for preparing these compounds have been devised. 

Oxazolidinediones are generally readily prepared from amino acids and hydroxy-amides with a carbonate equivalent such as carbonyldiimidazole or diethyl carbonate itself. Isothiocyanates can also be used as starting materials for the synthesis of 2,5-oxazolidinediones (Equation 25) <2006TL3953>. 

Scheme 12 shows the optical resolution of a-hydroxy ester rac-37, which was a key step in Takeda s synthesis of 2,4-oxazolidinedione 39 [71]. The compound... 

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