82780-50-5Relevant academic research and scientific papers
DIRECTED METALATION OF TERTIARY BENZAMIDES. SHORT SYNTHESES OF HYDRANGENOL AND PHYLLODULCIN
Watanabe, M.,Sahara, M.,Furukawa, S.,Billedeau, R.,Snieckus, V.
, p. 1647 - 1650 (1982)
Brief syntheses of isocumarin natural products hydragenol(2) and phyllodulcin(3) via ortho-lithiated benzamide intermediates are described.
SYNTHETIC APPROACH TO OPTICALLY ACTIVE 3-ARYL-3,4-DIHYDROISOCOUMARINS
Arnoldi, Anna,Bassoli, Angela,Merlini, Lucio,Ragg, Enzio
, p. 403 - 407 (2007/10/02)
Some optically active 3-aryl-3,4-dihydroisocoumarins have been obtained by enantioselective reduction of the corresponding aryl 2-carboxybenzyl ketones with the CBS catalyst.The ketones were obtained by the condensation of the o-toluate carbanion with ald
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.
