The Claisen Rearrangement in Aromatic Heterocyclic Compounds. I. The ortho-Claisen Rearrangement of Allyl, Methallyl, and Crotyl Ethers of 2-Methyl-4-quinolinol
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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.
- 公益社団法人日本薬学会の論文
- 1964-07-25
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