Whereas alkyl lithium and Grignard reagents both at rt and at -80°C thermally react with 3-methylisoxazolo[5,4-b]pyridine giving alkylation and/or isoxazole ring opening products, sodium malonate and sodium boron hydride react only under UV irradiation. Selective trappings of ketenimine or azirine intermediates give an enaminopyridone or two diasteroisomeric spiroaziridinopirydones. Regioselective opening of the aziridine ring with perchloric acid gives 3(1-amino-ethyl)-1H-pyridin-2-one. © 2002 Elsevier Science Ltd. All rights reserved.
Donati, D., Fusi, S., Ponticelli, F. (2002). Trapping of photochemical intermediates as a tool in organic synthesis. Preparation of spiroaziridinopyridones, a new heterocyclic system. TETRAHEDRON LETTERS, 43(52), 9527-9530 [10.1016/S0040-4039(02)02438-3].
Trapping of photochemical intermediates as a tool in organic synthesis. Preparation of spiroaziridinopyridones, a new heterocyclic system
Donati, Donato;Fusi, Stefania;Ponticelli, Fabio
2002-01-01
Abstract
Whereas alkyl lithium and Grignard reagents both at rt and at -80°C thermally react with 3-methylisoxazolo[5,4-b]pyridine giving alkylation and/or isoxazole ring opening products, sodium malonate and sodium boron hydride react only under UV irradiation. Selective trappings of ketenimine or azirine intermediates give an enaminopyridone or two diasteroisomeric spiroaziridinopirydones. Regioselective opening of the aziridine ring with perchloric acid gives 3(1-amino-ethyl)-1H-pyridin-2-one. © 2002 Elsevier Science Ltd. All rights reserved.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
https://hdl.handle.net/11365/4249
Attenzione
Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo