Formal Bimolecular [2 + 2 + 2] Cycloaddition Strategy for the Synthesis of Pyridines: Intramolecular Propargylic Ene Reaction/Aza Diels–Alder Reaction Cascades
| Autor: | Rick L. Danheiser, Philip J. Hamzik, Michiko Sasaki, Samuel G. Bartko, Hidaka Ikemoto |
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| Rok vydání: | 2018 |
| Předmět: |
Substitution reaction
010405 organic chemistry Chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Cycloaddition 0104 chemical sciences chemistry.chemical_compound Nucleophile Tosyl Intramolecular force Aza-Diels–Alder reaction Physical and Theoretical Chemistry Isomerization Ene reaction |
| Zdroj: | Organic Letters. 20:6244-6249 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | Two methods for the synthesis of multisubstituted pyridines are described. In each strategy, a highly reactive vinylallene is generated via an intramolecular propargylic ene reaction in the presence of an azadienophile. Reactions employing ethyl N-(tosyl)iminoacetate furnish an intermediate that undergoes elimination and isomerization upon the addition of DBU. The reaction of the intermediate vinylallene with TsCN leads to the isolation of a 2-sulfonylpyridine that serves as a versatile intermediate undergoing substitution reactions with oxygen and carbon nucleophiles. |
| Databáze: | OpenAIRE |
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