The thio-Claisen rearrangement of allyl 4-quinolyl sulfides

✍ Scribed by Yasuo Makisumi

• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 192 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70185-7

✦ Synopsis

It was reported in our previous papers (1) that, on heating at 2oo0, ally1 bquinolyl ethers were readily converted into the Claisen products, 3-allyl-4(1H)quinolones, in good yields accompanying small amounts of ring closure products, P,%dihydrofuro-[ 32-cjquinolines. H A ? or HBr-AcOH Several previous attempts ta bring about the Claisen Rearrangement in the ally1 phenyl sulfide system (thio-Claisen rearrangement*) have failed (2,3). It was recently reported, however, that heating of ally1 phenyl sulfide with quinoline or N,N-dimethylaniline afforded 2-methylthiacoumaran (4)ond thiachroman (5) and the formation of these products was interpreted as the results of cycliration of the initially formed normal Claisen product, 2-allylthiophenol, although an intermediacy of this compound was not confirmed. We wish to report a new example of the thia-Claisen rearrangement in ally1 4quinolyl sulfide and its derivatives. Ally1 4quinolyl sulfides (la and lb) were prepared in good yields by alkylation of * This name has been designated by Prof. Kwart (see ref. 8).