Tetrahedron

Synthesis of dihydro-1H-pyrrolo-and tetrahydropyrido [1, 2-a] indoles via a modified madelung reaction

W Verboom, EOH Orlemans, HJ Berga, HW Scheltinga…

Index: Verboom, W; Orlemans, E.O.M.; Berga, H.J.; Scheltinga, M.W.; Reinhoudt, D.N. Tetrahedron, 1986 , vol. 42, # 18 p. 5053 - 5064

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Citation Number: 29

Abstract

1-(2-Methylphenyl) lactams 9, having different electron-withdrawing groups at the benzylic position, cyclize under the influence of sodium hydride or potassium tert-butoxide. Depending on the ring size of the lactam moiety dihydropyrrolo-(10), tetrahydropyrido [1, 2- a] indole (11), or dihydro-1H-1-benzazeptne (12) derivatives are foraed. Pyrrolo [1, 2-a] indole 10c has been converted into the corresponding quinone 15b. Starting from ...