Intramolecular 1,3-Dipolar Cycloaddition Reactions Assisted by Microwaves

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Authors

POTÁČEK Milan POSPÍŠIL Jiří MAN Stanislav NEUSCHL Michal

Year of publication 2007
Type Article in Proceedings
Conference Book of Abstract, Advances in Synthetic and Medicinal Chemistry
MU Faculty or unit

Faculty of Science

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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