81428-86-6Relevant articles and documents
Metal-Free Addition of Benzyl Halides to Aldehydes Using Super Electron Donors: Access to 3,4-Dihydroisocoumarins and 1,2-Diarylethanols
Spitz, Cédric,Matteudi, Mélanie,Tintori, Guillaume,Broggi, Julie,Terme, Thierry,Vanelle, Patrice
, p. 15736 - 15742 (2020/12/23)
We report here the intermolecular metal-free addition reaction of functionalized benzyl halides to aldehydes using a super electron donor (SED). The metal-free and mild conditions allowed the formation of 3,4-dihydroisocoumarins and 1,2-diarylethanols with unprecedented functional group tolerance.
Oxidation of 3-arylisochromans by dimethyldioxirane. An easy route to substituted 3-arylisocoumarins
Bovicelli, Paolo,Lupattelli, Paolo,Crescenzi, Benedetta,Sanetti, Anna,Bernini, Roberta
, p. 14719 - 14728 (2007/10/03)
The selective oxidation of the two different benzylethereal position of 3-arylisochromans by dimethyldioxirane as a function of different substituents on the aromatic rings was studied. The easy oxidation of these compounds was exploited for a new easy ac
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.