Amino-Claisen Rearrangement. II. Quaternary Amino-Claisen Rearrangement of Anilinium Compounds with ortho Substituents
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Amino (N)-Claisen rearrangement of quaternary aniline derivatives with ortho substituents was investigated in relation to that of corresponding tertiary anilines. N-Allylated anilinium compounds 1 with a freely rotating ortho substituent such as a methyl or methoxy group yielded mostly the deallylated products 4 along with minor amounts of rearrangement products 2 and 3. The corresponding tertiary anilines yielded ortho rearrangement products 6 together with para ones 7. The quaternary N-Claisen rearangement of N-allylated 1,2,3,4-tetrahydroquinolinium salts 14 and indolinium salts 22 in which the ortho substituents are locked in rings afforded the ortho rearrangement products 15 and 23,respectively in good yields. N-Claisen rearrangement of the corresponding aromatic tertiary amines 18 also took place in good yield. The above rearrangements could be rationalized on the basis of mechanistic considerations.
- 社団法人日本薬学会の論文
- 1981-09-25
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