2,4,4,6-Tetrabromocyclohex-2,5-dien-1-one: 
An Excellent Reagent for Dibromination of Methyl at C-6 in Biginelli Compounds

Chem Sci Trans., 2012, 1(2), pp 329-334

DOI:10.7598/cst2012.213

Research Article

2,4,4,6-Tetrabromocyclohex-2,5-dien-1-one: An Excellent Reagent for Dibromination of Methyl at C-6 in Biginelli Compounds

Abstract

Biginelli compounds (ethyl 4-substituted-2-oxo-1,2,3,4-tetrahydropyrimidine-6-carboxylates) prepared from cyclodehydration of ethyl acetoacetate, urea and aromatic (or aliphatic) aldehydes have been subjected to bromination using (i) Br₂/CHCl₃ (ii) Br₂/AcOH and (iii) 2,4,4,6-tetrabromocyclohex-2-en-1-one (TBCO) separately. The last one viz., TBCO is found to be the best reagent in preparing the 6-dibromethyl derivative in terms of yield and green context.