Microwave assisted intramolecular 1,3-dipolar cycloaddition reactions and their stereochemistry

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Authors

POTÁČEK Milan POSPÍŠIL Jiří MAN Stanislav NEUSCHL Michal

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

Faculty of Science

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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