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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Shekinah A BassFenghai 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.

References

Jun 1, 1977·Journal of Medicinal Chemistry·K RamalingamD van der Helm
Jul 1, 1981·Journal of Medicinal Chemistry·M H HolshouserI H Hall
Feb 6, 1999·Bioorganic & Medicinal Chemistry Letters·D DhanakA West
Mar 2, 1999·Journal of the National Cancer Institute·M E BrackeM M Mareel
Aug 5, 2000·Journal of Natural Products·P G Pietta
Sep 6, 2002·Journal of Medicinal Chemistry·Peter NussbaumerAndreas Billich
Nov 26, 2002·The Journal of Organic Chemistry·Dallas K Bates, Kexue Li
Feb 6, 2004·Chemical & Pharmaceutical Bulletin·Yoshio AramakiMitsuru Shiraishi
Feb 23, 2005·Nature·Da Yu LinLawrence C Katz
Feb 1, 2007·Journal of the American Chemical Society·Liansuo ZuWei Wang
Apr 16, 2009·The Journal of Organic Chemistry·R Karl Dieter, Fenghai Guo
Dec 22, 2009·Organic & Biomolecular Chemistry·Benjamin WillyThomas J J Müller
Jun 8, 2011·Beilstein Journal of Organic Chemistry·Jonathan Clayden, Paul Maclellan
Jan 29, 2013·Journal of Agricultural and Food Chemistry·Nigel I JoyceJohn W van Klink
May 3, 2014·Accounts of Chemical Research·Kazuo TakimiyaMasahiro Nakano
Sep 26, 2014·Journal of Medicinal Chemistry·Brandon R SmithJon T Njardarson
Oct 28, 2014·Organic Letters·Tasuku InamiSeijiro Matsubara
Apr 10, 2015·Journal of the American Chemical Society·Yukihiro FukataSeijiro Matsubara
Jan 27, 2017·The Journal of Organic Chemistry·Pandi MuthupandiGovindasamy Sekar
Dec 1, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Esteban VargasWiston Quiñones

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Citations

May 7, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tania J BellingerFenghai Guo

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Methods Mentioned

BETA
column chromatography

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