Reaktion von 3‐Dimethylamino‐2,2‐dimethyl‐2H‐azirin mit Barbitursäure
作者:
Helmut Link,
Karl Bernauer,
John J. Daly,
Stanislav Chaloupka,
Heinz Heimgartner,
期刊:
Helvetica Chimica Acta
(WILEY Available online 1981)
卷期:
Volume 64,
issue 1
页码: 49-63
ISSN:0018-019X
年代: 1981
DOI:10.1002/hlca.19810640108
出版商: WILEY‐VCH Verlag GmbH
数据来源: WILEY
摘要:
Reaction of 3‐Dimethylamino‐2,2‐dimethyl‐2H‐azirine with Barbituric AcidThe reaction of 3‐dimethylamino‐2,2‐dimethyl‐2H‐azirine(1)with barbituric acid(4)in dimethyl formamide at room temperature yields a mixture of several compounds. The two main products5and6have been isolated in 40 and 10% yield, respectively, and their structures established by X‐ray analysis. InSchemes 4–6reaction mechanisms for the formation of5and6are postulated, the first step beeing either aC‐ or anN‐alkylation of barbituric acid.Reduction of5and6with NaBH4in ethanol at room temperature yields 6,6‐dimethyl‐1,5,6,7‐tetrahydro‐pyrrolo[2,3‐d]pyrimidin‐2,4(3H)‐dione(7)and 3,3‐dimethyl‐2,3‐dihydro‐imidazo[1,2‐c]pyrimidin‐5,7(1H, 6H)‐dione(8)in 38 and 48% yield, respectively. Treatment of6with 3Naqueous NaOH at room temperature gives 3,3‐dimethyl‐imidazo[1,2‐c]
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