Tetrahedron letters

New protocols for the synthesis of 3, 4-annulated and 4-substituted quinolines from β-bromo-α, β-unsaturated aldehydes and 1-bromo-2-nitrobenzene or 2- …

S Some, JK Ray, MG Banwell, MT Jones

Index: Some, Surajit; Ray, Jayanta K.; Banwell, Martin G.; Jones, Matthew T. Tetrahedron Letters, 2007 , vol. 48, # 20 p. 3609 - 3612

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Citation Number: 35

Abstract

The palladium [0]-mediated Ullmann cross-coupling of readily available β-bromo-α, β- unsaturated aldehydes of the general form 2 with 1-bromo-2-nitrobenzene (3, X= Br) delivers products, 4, that undergo reductive cyclization to novel quinolines (5) upon exposure to indium in aqueous ammonium chloride or to Raney-nickel in the presence of dihydrogen. Analogous cross-coupling of 2-bromoacetanilide (6) with 2 affords products of ...