Microwave assisted intramolecular 1,3-dipolar cycloaddition reactions and their stereochemistry
| Authors | |
|---|---|
| Year of publication | 2007 |
| Type | Article in Proceedings |
| Conference | Organic chemistry, present and future. International symposium organized in honour of Prof. Ghosez. |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | intramolecular cyclization; 1-3-dipolar cycloaddition; stereochemistry; microwaves |
| 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 and hexahydro-1H-pyrrolo[3,2-c]quinolines. 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, prepared in turn by N-alkylation of alkyl aminoacetates or other aminoderivatives with a EWG. The subsequent intramolecular cycloadditions gave the products in very good yields and selectivity. Their stereochemistry, influence of EWG and microwave in comparison with classical arrangement in a solvent upon the formation of product was searched. Further, generation of nitrones in intramolecular cycloaddition and their reactions were investigated. |
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