Efficient Regioselective Synthesis of 3,4,5-Trisubstituted 1,2,4-Triazoles on the Basis of a Lithiation–Trapping Sequence

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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 alpha,beta-unsaturated carbonyl compounds. The easy elaboration of such a group to phenol derivatives also provides greater flexibility in synthetic design.

Autore Pugliese

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  • PERNA F.;CAPRIATI V.

Titolo volume/Rivista

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Anno di pubblicazione

2014

ISSN

1099-0690

ISBN

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Numero di citazioni Wos

1

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Settori ERC

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Codici ASJC

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