Regioselective Synthesis of Methyl 2,3-Dihydro-2-aryl Benzofuran-3-Carboxylates Using Thallium(III) Nitrate
- 1 March 1993
- journal article
- research article
- Published by Taylor & Francis Ltd in Synthetic Communications
- Vol. 23 (5), 585-590
- https://doi.org/10.1080/00397919308009816
Abstract
Flavanones (1a–d) undergo smooth ring contraction with thallium(III) nitrate in presence of perchloric acid and trimethyl orthoformate resulting in the formation of methyl 2,3-dihydro-2-arylbenzofuran-3-carboxylates (2a–d) in good yields. The mechanism of this oxidation has also been discussed.Keywords
This publication has 8 references indexed in Scilit:
- Dehydrogenation of flavanones to flavones using thallium(III) acetate(TTA)Tetrahedron Letters, 1990
- One-step conversion of flavanones into isoflavones: a new facile biomimetic synthesis of isoflavonesTetrahedron Letters, 1990
- Oxidative 1,2-aryl rearrangement in flavanones using thallium(III)Tetrahedron Letters, 1990
- Oxidation of 4‐chromanones with thallium(III) nitrateJournal of Heterocyclic Chemistry, 1982
- Oxidation of Flavanones with Thallium(III) Nitrate(ttn). A Convenient Route to FlavonesSynthetic Communications, 1982
- Thallium in organic synthesis. 44. Oxidative rearrangements via oxythallation with thallium(III) nitrate supported on clayJournal of the American Chemical Society, 1976
- Thallium in organic synthesis. 43. Novel oxidative rearrangements with thallium(III) nitrate (TTN) in trimethyl orthoformate (TMOF)Journal of the American Chemical Society, 1976
- Configuration and conformation of 3-arylideneflavanonesThe Journal of Organic Chemistry, 1970