Photochemical synthesis of 3,4-dihydro-2H-1,3-oxazin-4-ones

被引：0
|
作者：
Wessig, P. [1 ]
Schwarz, J. [1 ]
Lindemann, U. [1 ]
Holthausen, M.C. [1 ]
机构：
[1] Institut für Organische und Bioorganische Chemie, Humboldt-Universität zu Berlin, Hessische Straße 1-2, 10115 Berlin, Germany
来源：
Synthesis | 2001年 / 08期
关键词：
Carbon - Carbonylation - Chemical bonds - Oxygen;
D O I：
10.1055/s-2001-15061
中图分类号：
学科分类号：
摘要：
The first example of a C - O bond formation in the course of the Norrish - Yang reaction is described. Starting with readily accessible α-mesyloxy-β-keto amides 4, a δ-hydrogen transfer to the excited carbonyl group occurs and the diradicals thus formed undergo a very rapid elimination of methane sulfonic acid providing enolate diradicals. These ambidental enolate diradicals undergo a regioselective cyclization to 3,4-dihydro-2H-1,3-oxazin-4-ones 5. In two cases a cleavage reaction is observed, giving cyclic imines. The mechanism is investigated by means of DFT- and ab initio methods.
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页码：1258 / 1262
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