The presence of an electron-donating methoxy group at the 4′-position of 4-phenyl-3,5-dimethyl-1,2,4-triazole is beneficial to lateral metalation/functionalization of this ring system once sBuLi is employed as the base and THF is used as the solvent at -78°C; this opens up an alternative approach towards the synthesis of several 1,2,4-triazole derivatives. Both carbon- and heteroatom-based halides are competent electrophiles for this transformation, as are aliphatic and aromatic aldehydes and ketones, isocyanates, carboxylic acid derivatives, and α,β-unsaturated carbonyl compounds. The easy elaboration of such a group to phenol derivatives also provides greater flexibility in synthetic design.
Efficient Regioselective Synthesis of 3,4,5-Trisubstituted 1,2,4-Triazoles on the Basis of a Lithiation-Trapping Sequence
Mansueto R.;Salomone A.;Perrone S.;
2014-01-01
Abstract
The presence of an electron-donating methoxy group at the 4′-position of 4-phenyl-3,5-dimethyl-1,2,4-triazole is beneficial to lateral metalation/functionalization of this ring system once sBuLi is employed as the base and THF is used as the solvent at -78°C; this opens up an alternative approach towards the synthesis of several 1,2,4-triazole derivatives. Both carbon- and heteroatom-based halides are competent electrophiles for this transformation, as are aliphatic and aromatic aldehydes and ketones, isocyanates, carboxylic acid derivatives, and α,β-unsaturated carbonyl compounds. The easy elaboration of such a group to phenol derivatives also provides greater flexibility in synthetic design.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
