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Reactions of 4-Imidazolidinone and 4-Imidazolinone Derivatives
El-Gawad, Ibrahim I. Abd,Harhash, Abd El-Hamid,Abou-Elzahab, Mohamed M. M.
, p. 481 - 483 (2007/10/02)
Treatment of 4-imidazolidinones (1) with dimethyl sulphate, acrylonitrile or acetic anhydride brings about N-alkylation or acylation to give 3.Hydrolysis of N-cyanoethyl derivatives (3f,g) affords the corresponding N-carboxyethyl derivatives (4a,b).Attempted cyclization of 4a with acetic anhydride gives 4-acetoxy-4-imidazolinone (6).Mannich reaction of 1 gives the N-Mannich bases (7).However, a similar reaction on 4 imidazolinones (2) affords the C-Mannich bases (8).The base 8a can be converted into S-(p-tolylthiomethyl) derivative (8h) by reaction with p-thiocre-sol.Reaction of Grignard reagents with 4-imidazolinones (2) affords 4-imidazolidinone derivatives (9).
