- SYNTHESIS OF DIHYDRO-1H-PYRROLO- AND TETRAHYDROPYRIDOINDOLES VIA A MODIFIED MADELUNG REACTION
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1-(2-Methylphenyl)lactams 9, having different electron -withdrawing groups at the benzylicposition, cyclize under the influence of sodium hydride or potassium tert-butoxyde.Depending on the ring size of the lactam moiety dihydropyrrolo- (10), tetrahydropyridoindole (11), or dihydro-1H-1-benzazepine (12) derivatives are formed.Pyrroloindole 10c has been converted into the corresponding quione 15b.Starting from naphthaleneacetonitrile 20, prepared in 5 steps from 2,3-dichloronaphthoquinone, the 5,10-dioxo-1H-pyrollobenzindole 22 is obtained upon treatment with base and subsequent oxidation of the protected hydroquinone function with ceric ammonium nitrate.
- Verboom, W,Orlemans, E.O.M.,Berga, H.J.,Scheltinga, M.W.,Reinhoudt, D.N.
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p. 5053 - 5064
(2007/10/02)
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- THE MADELUNG SYNTHESIS OF DIHYDRO-1H-PYRROLO- AND TETRAHYDROPYRIDO-INDOLES UNDER MILD CONDITIONS
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Benzeneacetonitriles substituted with lactam moieties in the ortho-position cyclize under the influence of a base, dependent on the ring-size of the lactam function, to dihydropyrrolo-,tetrahydropyridoindole or dihydro-1-benzazepin derivatives, respectively.
- Verboom, W.,Berga, W. P.,Trompenaars, W. P.,Reinhoudt, D. N.
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p. 685 - 688
(2007/10/02)
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