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Abstracts of Congress of Heterocyclic Chemistry | Regular issue | Vol 14, No. 10, 1980, pp.1649-1676
Published online, 1st January, 1970
DOI: 10.3987/R-1980-10-1649
Heterocycles via ortho-Lithiated Benzamides

Victor Snieckus*

*Guelph-Waterloo Centre for Graduate Work in Chemistry, University of Waterloo, Waterloo, Ontario, N2L 3G1, Canada

Abstract

Ortho-lithiated N,N-diethyl benzamides, readily generated by treatment of the corresponding amides with sec-BuLi or t-BuLi in THF or Et2O/TMEDA at -78°, are important new synthons (d3-reagents) for the regiospecific construction of highly substituted aromatic derivatives which are difficult to obtain by classical (usually electrophilic substitution) chemistry (Scheme 1). This paper will demonstrate the utility of ortho-lithiated benzamides for the synthesis of contiguously substituted aromatics, phthalide and isochroman-1,3-dione heterocycles, phthalideisoquinoline alkaloids, anthraquinone natural products, polycyclic anthraquinones and corresponding PAH’s, heterocyclic benzoquinones, and ellipticine alkaloids.