95217-41-7Relevant academic research and scientific papers
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
Expeditious synthesis of 3,4-dihydroisocoumarins and phthalides using the Heck-Matsuda reaction
Da Penha, Eduardo T.,Forni, José Augusto,Biajoli, André F.P.,Correia, Carlos Roque D.
scheme or table, p. 6342 - 6345 (2011/12/21)
Several 3,4-dihydroisocoumarins and phthalides were synthesized by an effective Heck-Matsuda reaction involving an ortho carboxybenzenediazonium salt with a series of styrenes bearing electron donating and electron withdrawing groups, methylvinyl ketone,
Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G
Mandal, Samir Kumar,Roy, Subhas Chandra
experimental part, p. 11050 - 11057 (2009/04/11)
A radical-promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp2TiCl) as the radical initiator. The total synthesis of four naturally occurring dihydrocoumarins hydrangenol, phyllodulcin, macrophyllol and thunberginol G has been accomplished using the radical technology. Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and Zn-dust in THF under argon.
Radical-mediated synthesis of 3,4-dihydroisocoumarins: total synthesis of hydrangenol
Mandal, Samir Kumar,Roy, Subhas Chandra
, p. 4131 - 4134 (2008/02/03)
A radically promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp2TiCl) as the radical initiator. The total synthesis of (±)-hydrangenol has been completed using this radical technology. Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and Zn-dust in THF under argon.
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.
