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Intramolecular Cycloadditions of Photogenerated Azaxylyleneswith Oxadiazoles Provide Direct Access to Versatile PolyheterocyclicKetopiperazines Containing a Spiro-oxirane Moiety.
- Source :
-
Organic Letters . Feb2015, Vol. 17 Issue 3, p438-441. 4p. - Publication Year :
- 2015
-
Abstract
- Photogeneratedazaxylylenes undergo intramolecular cycloadditionsto 1,3,4-oxadiazole pendants, which are accompanied by concomitantrelease of dinitrogen, yielding functionalized ketopiperazinoquinolinolscontaining an oxirane moiety fused to the quinolinole moiety whilespiro-connected to diketopiperazine. These primary photoproducts arereactive versatile intermediates which can be further derivatizedunder nucleophilic SN1- or SN2-like ring openingof the oxirane moiety. The oxidized quinolinones undergo new rearrangementsunder the conditions of the Schmidt reaction, leading to unprecedentedtriazacanoindolinones. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 17
- Issue :
- 3
- Database :
- Academic Search Index
- Journal :
- Organic Letters
- Publication Type :
- Academic Journal
- Accession number :
- 100857455
- Full Text :
- https://doi.org/10.1021/ol5033909