Journal
ORGANIC LETTERS
Volume 17, Issue 3, Pages 438-441Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol5033909
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Funding
- NSF [CHE-1362959]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1362959] Funding Source: National Science Foundation
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Photogenerated azaxylylenes undergo intramolecular cycloadditions to 1,3,4-oxadiazole pendants, which are accompanied by concomitant release of dinitrogen, yielding functionalized ketopiperazinoquinolinols containing an oxirane moiety fused to the quinolinole moiety while spiro-connected to diketopiperazine. These primary photoproducts are reactive versatile intermediates which can be further derivatized under nucleophilic S(N)1- or S(N)2-like ring opening of the oxirane moiety. The oxidized quinolinones undergo new rearrangements under the conditions of the Schmidt reaction, leading to unprecedented triazacanoindolinones.
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