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 previ
Thio-claisen rearrangement of allyl 3-quinolyl sulfides
β Scribed by Yasuo Makisumi; Akira Murabayashi
- Publisher
- Elsevier Science
- Year
- 1969
- Tongue
- French
- Weight
- 179 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0040-4039
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Earlier, we reported that the thio-Cloisen reorrongement of ally1 4quinolyl sulfides (I) to 2,3-dihydrothieno[3.2-clquinolines (III) proceeded through the prototropic cyclizotion of the initially formed 3-allyl-4(1 H)-quinolinethiones (II), on the basis of the quantitative transformation of II into
A number of studies hove established that a great deal of specificity is observed in the direction of Claisen rearrangement and this specificity has been interpreted on the basis of bond structure (1) or electronic structure (2) of the parent aromatic nucieus. Our previous works (3,4) on the thermal