2674-45-5Relevant articles and documents
Synthesis of 3,4-Dihydroisocoumarins from α-Lithiated o-Toluates
Ollero,Castedo,Domínguez
, p. 1047 - 1048 (1997)
Tellurides 2 prepared from α-bromo-o-toluesters 1 undergo lithium-tellurium exchange to give benzylic anions that can be condensed with aldehydes or ketones to afford 3,4-dihydroisocoumarins 3.
A Photocatalytic Meerwein Approach to the Synthesis of Isochromanones and Isochromenones
Crespi, Stefano,J?ger, Stefanie,K?nig, Burkhard,Fagnoni, Maurizio
, p. 2147 - 2153 (2017/04/24)
A visible-light RuII photoredox Meerwein synthesis of isochromanones and isochromenones is described starting from diazonium salts of differently substituted anthranilic acids and various alkenes. This approach has allowed the reliable and effi
Photoinduced Molecular Transformations. Part 137. New General Synthesis of 3-Substituted 3,4-Dihydro-1H-benzopyran-1-ones (3,4-Dihydroisocoumarins) via Radical and Photochemical Fragmentations as the Key Step
Kobayashi, Kazuhiro,Konishi, Atsushi,Kanno, Yoshikazu,Suginome, Hiroshi
, p. 111 - 116 (2007/10/02)
A new general method for a two-step synthesis of 3-substituted 3,4-dihydro-1H-benzopyran-1-ones (3,4-dihydroisocoumarins) is described.This method involves either regioselective alkoxyl radical fragmentation or regioselective photochemical fragmentation as the key step. 2-Hydroxyalkylation of a lithiated o-tolyl tert-butyl ketone with aromatic and aliphatic aldehydes and ketones gave equilibrated mixtures of 1-tert-butyl-3,4-dihydro-1-hydroxy-3-alkyl (or 3-aryl)-1H-2-benzopyrans and their ring-opened isomers in 42-94percent yield.Photolysis of mixtures in chloroform withPyrex-filtered light gave 3-alkyl (or 3-aryl)-3,4-dihydro-1H-benzopyran-1-ones (3,4-dihydroisocoumarins) in 27-64percent yield as exclusive isolable products.On the other hand, photolysis of hypoiodites of the equilibrated mixture in benzene containing mercury(II) oxide and iodine gave the 3-substituted dihydroisocoumarins in 37-64 percent yield with an accompanying formation of phthalide, arising from a radical cascade process triggered by β-scission of the alkoxyl radicals generated from the ring-opened isomer of the lactones.The formation mechanisms of all the products are discussed.