A Ring Expansion−Annulation Strategy for the Synthesis of Substituted Azulenes. Preparation and Suzuki Coupling Reactions of 1-Azulenyl Triflates
| Autor: | Kevin M. Shea, Aimee L. Crombie, Rick L. Danheiser, John L. Kane |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
Annulation
Molecular Structure Chemistry Antiulcer drug Anti-Inflammatory Agents Non-Steroidal Organic Chemistry chemistry.chemical_element Benzene Ketones Anti-Ulcer Agents Ring (chemistry) Biochemistry Combinatorial chemistry Azulenes Rhodium Suzuki reaction Intramolecular force Humans Cycloheptanes Physical and Theoretical Chemistry Sesquiterpenes Trifluoromethanesulfonate Carbenoid |
| Zdroj: | Organic Letters. 3:1081-1084 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol0156897 |
| Popis: | [structure: see text]. A new strategy for the synthesis of substituted azulenes is reported, based on the reaction of beta'-bromo-alpha-diazo ketones with rhodium carboxylates. The key transformation involves intramolecular addition of a rhodium carbenoid to an arene pi-bond, electrocyclic ring opening, beta-elimination, tautomerization, and trapping to produce 1-hydroxyazulene derivatives. The synthetic utility of the method is enhanced by the ability of the triflate derivatives to participate in Suzuki coupling reactions, as illustrated in a synthesis of the antiulcer drug egualen sodium (KT1-32). |
| Databáze: | OpenAIRE |
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