Tetrahedron Letters

Syntheses of phenanthridines and benzophenanthridines by intramolecular ortho-arylation of aryl amide ions with aryl halides via S RN 1 reactions

ME Budén, RA Rossi

Index: Buden, Maria E.; Rossi, Roberto A. Tetrahedron Letters, 2007 , vol. 48, # 49 p. 8739 - 8742

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Citation Number: 28

Abstract

The photostimulated reaction of N-(2-halo-benzyl) aryl amines with t-BuOK in liquid ammonia affords fused azaheterocycles by the SRN1 mechanism. The starting materials are easily obtained by the reaction of 2-halo-benzyl chloride and aromatic amines to prepare the secondary amines. Through this approach, phenanthridine (90%), 4-phenylphenanthridine (87%), benzo [a] phenanthridine (98%), and benzo [c] phenanthridine (84%) were ...