16078-34-5Relevant articles and documents
Palladium-Catalyzed Direct and Specific C-7 Acylation of Indolines with 1,2-Diketones
Xie, Guilin,Zhao, Yuhan,Cai, Changqun,Deng, Guo-Jun,Gong, Hang
, p. 410 - 415 (2021)
The indole scaffold is a ubiquitous and useful substructure, and extensive investigations have been conducted to construct the indole framework and/or realize indole modification. Nevertheless, the direct selective functionalization on the benzenoid core must overcome the high activity of the C-3 position and still remains highly challenging. Herein, a palladium-catalyzed direct and specific C-7 acylation of indolines in the presence of an easily removed directing group was developed. This strategy usually is considered as a practical strategy for the preparation of acylated indoles because indoline can be easily converted to indole under oxidation conditions. In particular, our strategy greatly improved the alkacylation yield of indolines for which only an unsatisfactory yield could be achieved in the previous studies. Furthermore, the reaction can be scaled up to gram level in the standard reaction conditions with a much lower palladium loading (1 mol %).
Regioselective Friedel-Crafts Acylation of 1,2,3,4-Tetrahydroquinoline and Related Nitrogen Heterocycles: Effects of NH Protective Groups and Ring Size
Ishihara, Yuji,Tanaka, Toshimasa,Goto, Giichi
, p. 3401 - 3406 (2007/10/02)
Regioselectivity of the Friedel-Crafts acylation of the following nitrogen heterocyles was studied: 2,3-dihydro-1H-indoles 3, 1,2,3,4-tetrahydroquinolines 4, 2,3,4,5-tetrahydro-1H-1-benzazepines 5 and 1,2,3,4,5,6-hexahydro-1-benzazocines 6.It was found that though the ratio of regioisomers depends on ring size, it can be controlled by changing the NH protective groups.A molecular orbital (MO) calculation of the Lewis acid co-ordinated substrates gave a rational explanation of the regioselectivity.
Synthese d'(indolyl-3)-4 dihydro-2,5 furanonnes-2 hydrosolubles
Baron, Michel,Cointet, Paul de,Bauduin, Gerard,Pietrasanta, Yves,Pucci, Bernard
, p. 249 - 256 (2007/10/02)
Une cyclisation du type Dieckmann suivie d'une decarboxylation permet d'acceder directement aux (indolyl-3)-4 dihydro-2,5 furanonnes-2 acetylees ou non sur l'homocycle a partir des ethoxycarbonylacetoxyacetyl-3 indoles correspondants sans protection prealable de la position 1 du cycle indolique et du substituant acyle de l'homocycle.
