Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications

二烷基铜酸锂与硫色满酮的共轭加成反应的发展:2-烷基硫色满-4-酮的合成及其他合成应用

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作者:Shekinah A Bass, Dynasty M Parker, Tania J Bellinger, Aireal S Eaton, Angelica S Dibble, Kaata L Koroma, Sylvia A Sekyi, David A Pollard, Fenghai Guo

Abstract

Lithium dialkylcuprates undergo conjugate addition to thiochromones to afford 2-alkylthiochroman-4-ones in good yields. This approach provide an efficient and general synthetic approach to privileged sulfur-containing structural motifs and valuable precursors for many pharmaceuticals, starting from common substrates-thiochromones. Good yields of 2-alkyl-substituted thiochroman-4-ones are attained with lithium dialkylcuprates, lithium alkylcyanocuprates or substoichiometric amount of copper salts. The use of commercially available inexpensive alkyllithium reagents will expedite the synthesis of a large library of 2-alkyl substituted thiochroman-4-ones for additional synthetic applications.

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