Abstract
The thermal rearrangement of allyl, methallyl, and crotyl ethers (Ia, Ib, and Ic) of 2-methyl-4-quinolinol was investigated and the ortho-Claisen rearrangement products (IIa, IIb, and IIc) with the inversion of the migrating group and their consecutive intramolecular cyclization products, the 2, 3-dihydro [3, 2-c] quinoline derivatives (IIIa, IIIb, and IIIc) were obtained. No detectable amounts of the 1-allyl-2-methyl-4(1H)-quinolones resulting from the alkyl rearrangement were formed. The different results between the thermal rearrangement of the allyl 2-methyl-4-quinolyl ethers and that of the 7-allyloxy-s-triazolo [1, 5-α] pyrimidines were discussed.
