36149-35-6Relevant academic research and scientific papers
Ring-chain tautomerism. Part 9.1 2-Acylbenzamides, 8-acyl-1-naphthamides and 5-acyl-4-phenanthramides
Bowden, Keith,Hiscocks, Simon P.,Perjessy, Alexander
, p. 291 - 295 (2007/10/03)
Ring-chain tautomerism in N-methyl- and N-(substituted phenyl)-2-formylbenzamides, 2-benzoylbenzamides, 8-formyl-1-naphthamides, 8-benzoyl-1-naphthamides and 5-formyl-4-phenanthramides has been investigated by IR and 1H NMR spectroscopy and the measurement of their pKa values in 30% (v/v) dimethyl sulfoxide-water. The tautomeric pair synthesised, i.e. hydroxylactamacylamide or aminolactone-iminocarboxylic acid, appears to be a function of the method of preparation and/or the basicity of amine used. The cyclic tautomer, i.e. hydroxylactam or aminolactone, is predominant in all cases studied. However, equilibrium constants have been estimated from the pKa values for aminolactone-iminocarboxylic acid tautomerisation in which the effect of the links follow similar trends as found for the corresponding hydroxylactone-acylcarboxylic acid tautomeric systems.
Preparation of 3-Hydroxyindolin-1-ones and o-Acylbenzamides. A Study of Ring-Chain Tautomerism
Nishio, Takehiko,Yamamoto, Hiroshi
, p. 883 - 892 (2007/10/02)
3-Hydroxyisoindolinones (ring form) as well as their chain tautomers, o-acylbenzamides, were prepared from the reactions of 3-benzalphthalide 1, 3-halophthalides 3, and o-acylbenzoic acids 6 or their esters 7 with amines 2, and those of phthalimides 4 wit
