- Regioselective Friedel-Crafts Acylation of 1,2,3,4-Tetrahydroquinoline and Related Nitrogen Heterocycles: Effects of NH Protective Groups and Ring Size
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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.
- Ishihara, Yuji,Tanaka, Toshimasa,Goto, Giichi
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p. 3401 - 3406
(2007/10/02)
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