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Synthese der isomeren 3, 4‐Dimethyl‐4‐phenyl‐3, 4‐dihydro‐carbostyrile

 

作者: J. Schmutz,   F. Künzle,  

 

期刊: Helvetica Chimica Acta  (WILEY Available online 1970)
卷期: Volume 53, issue 1  

页码: 89-94

 

ISSN:0018-019X

 

年代: 1970

 

DOI:10.1002/hlca.19700530110

 

出版商: WILEY‐VCH Verlag GmbH

 

数据来源: WILEY

 

摘要:

AbstractCyclisation of 2‐methyl‐3‐phenyl‐but‐3‐en‐anilide (III) with polyphosphoric acid gavecis‐3, 4‐dimethyl‐4‐phenyl‐3, 4‐dihydro‐carbostyril (VII) in 61% yield together with a small amount of 2, 3‐dimethylindenone (VIII), whereas with AlCl3a phenyl group was split off to give 3, 4‐dimethylcarbostyril (VI). The anilide III isomerises tocis‐ andtrans‐2, 3‐dimethyl‐cinnam‐anilide (IV resp. V) under basic conditions.The anilides IV and V gave only small yields of the dihydrocarbostyril VII with polyphosphoric acid. Chlorination of VII in position 3 using PCl5yielded IX which, on splitting out HCl, gave 3‐methylene‐4‐methyl‐4‐phenyl‐3, 4‐dihydro‐carbostyril (X). X was converted totrans‐3, 4‐dimethyl‐4

 

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