98117-19-2Relevant academic research and scientific papers
Cumulated Ylides, XVII. Synthesis of Cyclic Compounds from Triphenylphosphorane and Oxocarboxylic Acids - A Novel Method for Anellation
Bestmann, Hans Juergen,Schade, Gerold,Luetke, Harry,Moenius, Thomas
, p. 2640 - 2658 (2007/10/02)
By entropically supported intramolecular Wittig reaction from α-keto carboxylic acids 23 with triphenylphosphorane (1) N-phenylmaleinisoimides 26 and -imides 29 are formed.The compounds 26 can be rearranged into 29 with a catalytic amount of sodium azide. - From γ-keto carboxylic acids 30 3-substituted 2-cyclopenten-1-ones 37 can be derived via the 3,6-dioxo-2-(triphenylphosphoranylidene)alkananilides 33.Analogously, 3-substituted 2-cyclohexen-1-ones 49 are formed from δ-keto carboxylic acids 46. o-Acylbenzoic acids 38, in the case R = H, are converted with 1 into the benzazepinedione derivative 44, and in the case R unlike H into 3-substituted 1-oxo-1H-indene-2-carboxanilides 45. - Starting from oxo carboxylic acids, possessing the carbonyl function in a ring, five- and six-membered rings can be anellated in a simple way.
