2012年7月
STUDIES ON THE PETASIS REACTION OF 2-PYRIDINECARBALDEHYDE DERIVATIVES AND ITS PRODUCTS
HETEROCYCLES
- ,
- ,
- 巻
- 85
- 号
- 7
- 開始ページ
- 1655
- 終了ページ
- +
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.3987/COM-12-12500
- 出版者・発行元
- PERGAMON-ELSEVIER SCIENCE LTD
The Petasis reaction of various 2-pyridinecarbaldehydes with secondary amines and boronic acids in refluxed acetonitrile proceeded to afford desired products up to 96% yield. The reaction proceeded under mild conditions to afford wide range of amines adjacent to heteroaromatic rings. Interestingly, the aldehyde possessing a nucleophilic moiety, 4-(dimethylamino)-2-pyridinecarbaldehyde, with (S)-(-)-N-methyl-1-phenylethylamine and 2 equivalent of trans-2-phenylvinylboronic acid afforded unexpected product, (E)-N-benzyl-3-phenyl-1-(pyridin-2-yl)prop-2-en-1-amine, in high yield. This product might be formed through the direct alkylation of aldehyde by trans-2-phenylvinylboronic acid, followed by anion/enolate isomerization. Derivatization of the Petasis products were also employed and 2-alkyl substituted pyridine derivatives can be obtained through deamination of the Petasis products under the simple hydrogenation conditions.
- リンク情報
- ID情報
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- DOI : 10.3987/COM-12-12500
- ISSN : 0385-5414
- Web of Science ID : WOS:000307206100007