92874-01-6Relevant academic research and scientific papers
Synthesis of 3-arylisocoumarins by using acyl anion chemistry and synthesis of thunberginol A and cajanolactone A
Sudarshan, Kasireddy,Manna, Manash Kumar,Aidhen, Indrapal Singh
, p. 1797 - 1803 (2015/05/27)
A new strategy for the synthesis of 3-arylisocoumarins and 8-hydroxy-3-arylisocoumarins was investigated by using acyl anion chemistry for the initial C-C bond formation. The obtained keto esters and keto lactones as intermediates underwent based-promoted intramolecular cyclization to afford 3-arylisocoumarins in good yields. The developed methodology was applied for the synthesis of the important natural products thunberginol A and cajanolactone A.
Synthesis of some new 3-(chlorophenyl)isocoumarins and their conversion to 3,4-dihydro derivatives
Rama, Nasim H.,Iqbal,Rauf,Rao, Muhammad I.,Zamani,Raza, Abdul R.
, p. 338 - 341 (2007/10/03)
Condensation of homophthalic acid 4 with chlorobenzoyl chlorides 5a-c yields 3-(chlorophenyl)isocoumarins 6a-c which on alkaline hydrolysis give the keto-acids 7a-c. (dl)-3-(Chlorophenyl)-3,4-dihydroisocoumarins 10a-c have been obtained by the reduction of 7a-c to racemic hydroxyacids 9a-c followed by cyclodehydration using acetic anhydride.
Reactions of carbonyl compounds in basic solutions. Part 21. The mechanisms of the alkaline hydrolysis of substituted methyl 2-(2-oxopropyl)- and 2-(2-oxo-2-phenylethyl)-benzoates and 2-(2-acetylphenyl)- and 2-(2-benzoylphenyl)-acetates
Bowden, Keith,Byrne, Jane M.
, p. 2203 - 2206 (2007/10/03)
Rate coefficients have been measured for the alkaline hydrolysis of methyl 2-[2-oxo-2-(3- or 4-substituted phenyl)ethyl]benzoates, 2-[2-(3- or 4-substituted benzoyl)phenyl]acetates,2-(2-oxopropyl) and 2-(1,1-dimethyl-2- oxopropyl)benzoates, 2-(2-acetylphenyl)acetate and 2-(2-acetylphenyl)-2,2- dimethylacetates in 70% (v/v) dioxane-water at 30.0 °C. Those for the six parent esters were also measured at 45.0 and 60.0 °C and the enthalpies and entropies of activation have been evaluated. The relative rates of hydrolysis, activation parameters and substituent effects have been used to demonstrate neighbouring participation by the keto-carbonyl groups in the alkaline hydrolysis of the esters under study. For comparable systems, participation by six-membered ring intermediates appears somewhat less advantageous than five-membered.
