Intramolecular 1,3-Dipolar Cycloaddition Reactions Assisted by Microwaves
| Authors | |
|---|---|
| Year of publication | 2007 |
| Type | Article in Proceedings |
| Conference | Book of Abstract, Advances in Synthetic and Medicinal Chemistry |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | microwaves; intramolecular cyclization; 1,3-dipolar cycloaddition |
| Description | We have investigated intramolecular microwave - assisted 1,3-dipolar cycloaddition reactions of in situ generated azomethine ylides leading to hexahydrochromeno[4,3-b]pyrroles [3,4] and hexahydro-1H-pyrrolo[3,2-c]quinolines 3 [5]. A simple protocol was developed for these reactions, whereby the ylides were generated under microwave irradiation by the reaction of ortho-(3-alkenyl) oxybenzaldehydes or ortho-(3-alkenyl)aminobenzaldehydes with secondary amines 2, prepared in turn by N-alkylation of alkyl aminoacetates or other aminoderivatives with an EWG. The subsequent intramolecular cycloadditions gave the products 3 in very good yields and selectivity. Their stereochemistry, influence of EWG and microwaves in comparison with classical arrangement in a solvent upon the formation of product was searched. |
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