Tetrahedron

New strategies for the synthesis of heteroannulated 2-pyridinones, substituted 2-quinolinones and coumarins from dehydroamino acid derivatives

MJRP Queiroz, AS Abreu, RC Calhelha, MSD Carvalho…

Index: Queiroz, Maria Joao R.P.; Abreu, Ana S.; Calhelha, Ricardo C.; Carvalho, M. Solange D.; Ferreira, Paula M.T. Tetrahedron, 2008 , vol. 64, # 22 p. 5139 - 5146

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Citation Number: 24

Abstract

Several heteroannulated pyridinones were prepared from the methyl esters of N-Boc-β, β- diheteroaryldehydroalanines by treatment with acetic acid. The latter were obtained by a bis- Suzuki coupling of a β, β-dibromodehydroalanine with heteroarylboronate compounds. The products were obtained in good yields and the cyclization reaction involves the nucleophilic attack of one of the heteroaromatic rings on the carbonyl of the Boc group. The scope of ...