149990-86-3Relevant articles and documents
OXALYLMETHYLENEPHOSPHORANES. 1. REACTIONS OF ETHYL TRIPHENYLPHOSPHORANYLIDENEPYRUVATE AND TRIPHENYLPHOSPHORANYLIDENEPYRUVIC ACID HYDRAZIDE WITH 5-ARYL-2,3-FURANDIONES
Kozminykh, V. O.,Igidov, N. M.,Kozminykh, E. N.,Berezina, E. S.
, p. 191 - 198 (2007/10/02)
Ethyl triphenylphosphoranylidenepyruvate (1) readily reacts with 5-aryl-2,3-furandiones (2) to afford the deeply coloured resonance stabilized cyclic oxalyl ylides (3) being inactive towards aldehydes.Once a small amount of the competitive Wittig product - 2-ethoxalyl-5-phenyl-3(2H)-furanone (4a) besides the corresponding phosphorane (3a) has been obtained.However triphenylphosphoranylidenepyruvic acid hydrazide (8) when treated with 5-aryl-2,3-furandiones (2) gives only aroylpyruvoylhydrazides (10), which can be converted to 3-pyrazolcarboxylic acid hydrazides (13).A possible mechanism of the reaction of ylide (1) with 2,3-furandiones (2) is proposed. Key words: Ethyl triphenylphosphoranylidenepyruvate; triphenylphosphoranylidenepyruvic acid hydrazide; reactions with 5-aryl-2,3-furandiones; 1-triphenylphosphoranylidene-4-cyclopentene-2,3-diones; oxalyl ylides; reactivity towards carbonyl reagents.