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- Title
One-Pot Synthesis of 4-Substituted 3,4-Dihydro-3-methoxyisocoumarins via Carboxylation of α-Substituted 2-Lithio- β-methoxystyrenes with Carbon Dioxide.
- Authors
Kobayashi, Kazuhiro; Nagaoka, Toshiyuki; Shirai, Yuu; Miyatani, Wataru; Yokoi, Yuki; Konishi, Hisatoshi
- Abstract
A new type of isocoumarins (=1 H-isochromen-1-ones=1 H-2-benzopyran-1-ones), 4-substituted 3,4-dihydro-3-methoxyisocoumarins 2, can be obtained by a one-pot process from α-substituted 2-bromo- β-methoxystyrenes 1. Thus, lithium 2-(1-aryl(or methyl)-2-methoxyethenyl)benzoates are conveniently generated via the Br/Li exchange between 1 and BuLi, followed by the action of CO2 on the resulting α-substituted 2-lithio- β-methoxystyrenes. Upon treating with concentrated HCl at room temperature, these lithium benzoates undergo lactonization to provide the desired 3,4-dihydroisocoumarins 2 in relatively good yields.
- Subjects
ISOCOUMARINS; BENZOPYRANS; HETEROCYCLIC compounds; LITHIUM; BENZOATES
- Publication
Helvetica Chimica Acta, 2012, Vol 95, Issue 2, p191
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201100297