Journal of Organic Chemistry p. 742 - 747 (1984)
Update date:2022-09-26
Topics:
Watanabe, Mitsuaki
Sahara, Masanori
Kubo, Masaki
Furukawa, Sunao
Billedeau, R. J.
Snieckus, V.
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.
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Doi:10.1021/jo00200a048
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(1984)