Synthesis

Lithiation and side-chain substitution of 3-alkyl-1H-quinoxalin-2-ones

K Smith, GA El-Hiti, SA Mahgoub

Index: Smith, Keith; El-Hiti, Gamal A.; Mahgoub, Safaa A. Synthesis, 2003 , # 15 p. 2345 - 2348

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Citation Number: 21

Abstract

Abstract 3-Methyl-1H-quinoxalin-2-one has been doubly lithiated with n-butylithium at-78 C in THF. The dilithio reagent thus obtained reacts with various electrophiles (iodomethane, iodoethane, D 2 O, benzaldehyde, benzophenone, cyclohexanone) to give modified 3- substituted 1H-quinoxalin-2-ones in good yields. In the reaction of the dilithio reagent with phenyl isothiocyanate the product was a tautomer of the simple substitution product. ...