85164-36-9Relevant academic research and scientific papers
Ortho-Lithiated Tertiary Benzamides. Chain Extension via o-Toluamide Anion and General Synthesis of Isocoumarins Including Hydrangenol and Phyllodulcin
Watanabe, Mitsuaki,Sahara, Masanori,Kubo, Masaki,Furukawa, Sunao,Billedeau, R. J.,Snieckus, V.
, p. 742 - 747 (2007/10/02)
Lithiation of N,N-diethyl-2-methylbenzamide (2a) followed by condensation with aromatic aldehydes and basic hydrolysis leads to 3-aryl-3,4-dihydroisocoumarins 4 in modest overall yields.Adoption of this methodology to N,N-dimethyl-2-methyl-6-methoxybenzamide (7b) provides isocoumarins 9a and 9b which by selective demethylation procedures yields hydrangenol (10a) and phyllodulcin (10c), naturally occurring isocoumarins of pharmacological interest.A one-pot, abbreviated procedure for the preparation of both 9a and 9b starting with N,N-Dimethyl-2-methoxybenzamide (6c) is also described.
Formation od some 3-Aryl-3,4-dihydroisocoumarins by Thermal Ring Closure of Stilbene-2-carboxylic Acids
Bellinger, Geoffrey C. A.,Campbell, William E.,Giles, Robin G. F.,Tobias, Julius D.
, p. 2819 - 2826 (2007/10/02)
When heated at 200 deg C, cis- and trans-4'- and 2'-methoxystilbene-2-carboxylic acids have been converted into the title compounds in varying yields, as has trans-4'-hydroxystilbene-2-carboxylic acid.On the other hand, trans-4'-nitrostilbene-2-carboxylic acid affords 3-(4-nitrobenzyl)phthalide.Mass spectrometry provides a simple method of distinguishing between the dihydroisocoumarins and phthalides.
