2012年1月
Phosphane-free Pd 0-catalyzed cycloamination and carbonylation with Pd(OAc) <inf>2</inf> and Cu(OAc) <inf>2</inf> in the presence of K <inf>2</inf>CO <inf>3</inf>: Preparation of benzocyclic amines and benzolactams
European Journal of Organic Chemistry
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- 巻
- 号
- 2
- 開始ページ
- 366
- 終了ページ
- 379
- 記述言語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/ejoc.201101214
Phosphane-free Pd 0-catalyzed intramolecular aromatic amination was studied. o-Halophenethylamines and 3-(o-halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc) 2 and Cu(OAc) 2 in the presence of K 2CO 3. Application of the method to substrates containing isoquinoline rings- the 1-(o-bromobenzyl)-3,4-dihydroisoquinolines 6, the 1-(o-bromobenzyl)-1,2,3,4-tetrahydroisoquinolines 7, and the 1-(o-bromophenethyl)isoquinolines 9- provided the indolo[2,1-a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β-carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3-a] indolizine-13-ones 15 and the benz[f]indolo[2,3-a]quinolizine 18. The benzo[f]pyrido[3,4-a]indolizine and indolo[f]pyrido[3,4-a]indolizin-12-one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1-a][2,7]naphthyridine 34 and the indolo[2,3-a]pyrido[g]quinolizin-8-one 36 [(±)-dihydronaucléfine] in good yields. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
- リンク情報
- ID情報
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- DOI : 10.1002/ejoc.201101214
- ISSN : 1434-193X
- eISSN : 1099-0690
- SCOPUS ID : 84855173469