Microwave-assisted Solvent-free Intramolecular 1,3-Dipolar Cycloaddition Reactions Leading to Hexahydrochromeno[4,3-b] pyrroles: Scope and Limitations
| Authors | |
|---|---|
| Year of publication | 2006 |
| Type | Article in Periodical |
| Magazine / Source | Tetrahedron |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | Intramolecular cycloaddition; Azomethine ylides; Solventfree synthesis; Microwave assisted synthesis; 1-3 Dipolar cycloaddition |
| Description | We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15 to 40 min in 16-90% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. |
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