Recent Advances in the Decarboxylative Acylation/Cyclization of α-Keto Acids

doi:10.6023/cjoc202205025

Abstract

Decarboxylation of α-keto acids is a simple and efficient method to obtain corresponding acyl radicals. Cascade radical cyclization has been proved as efficient approach towards cyclic structures, especially heterocyclic ones. A variety of acylated cyclic compounds such as indolones, quinolinones, phenanthridines, coumarins, chromones, benzothiophenes, and pyrrole[1,2-a]indoles could be constructed using α-keto acids via the decarboxylative acylation/cyclization with acyl radicals as intermediates. This review focuses on the recent advances in the acylation/cyclization reaction triggered by acyl radicals that formed from the decarboxylation of α-keto acids.

Key words: α-keto acids, cyclization reaction, radical reaction, acylation

Cite this article

Yechun Wu, Jintao Yu. Recent Advances in the Decarboxylative Acylation/Cyclization of α-Keto Acids[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3606-3619.

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Fig. & Tab. 33

Scheme 1. AgNO3-catalyzed reaction of N-aryl acrylamides with α-keto acids towards acylated oxindoles

Scheme 2. Synthesis of C-3 acylated dihydroquinolinone from cinnamamides and α-keto acids catalyzed by AgNO3

Scheme 3. AgNO3-catalyzed synthesis of C-3 acylated quinolinones and dihydroquinolinones from α-keto acids and N-aryl cinnamylamides

Scheme 4. Silver-catalyzed synthesis of 6-acyl phenanthridines from 2-isocyanobiphenyl and α-oxocarboxylates

Scheme 5. Silver-mediated radical cyclization of alkynoates and α?keto acids towards 3-acylated coumarins

Scheme 6. Radical 5-exo cyclization of alkynoates and α-keto acids towards 3-acylated coumarins

Scheme 7. Silver-catalyzed cascade reaction of o-cyanoarylacrylamides and α-keto acids towards acylated quinoline-2,4-diones

Scheme 8. AgNO3-catalyzed cascade decarboxylation and oxidative cyclization toward dihydroflavonoids

Scheme 9. Synthesis of 3-acylbenzothiophenes via radical cyclization of 2-alkynylthioanisoles with α-keto acids

Scheme 10. Silver-catalysed decarboxylative cross-coupling of α-keto acids with ortho-hydroxyarylenaminones towards 3-acylchromones

Scheme 11. Decarboxylative cyclization of α-keto acids with 2-cyano-3-arylaniline acrylamides

Scheme 12. Ag-catalyzed synthesis of 3,4-dihydroquinolinones from oxalic acids and alkenes

Scheme 13. Silver-catalyzed decarboxylative radical addition/cyclization towards quinolin-2-ones

Scheme 14. Synthesis of 3?acyl-spiro[4,5]trienones via silver-catalyzed decarboxylative acylation and ipso-cyclization

Scheme 15. Synthesis of mono- and diacylated pyrro[1,2-a]indoles from of N-propynylindoles and α-keto acids

Scheme 16. Silver-catalyzed decarboxylative aminoformylation towards azaheterocyclic acetamides

Scheme 17. Synthesis of pyrro[1,2-a]indole from N-allyl indole and α-carbonyl acid catalyzed by silver

Scheme 18. Silver-catalyzed oxidative C—C σ-Bond acylation/arylation of alkylidenecyclopropanes towards 2-acyl-3,4-dihydronaph- thalenes

Scheme 19. Palladium-catalyzed decarboxylative ortho-amida- tion of O-methyl ketoximes with oxamic acids

Scheme 20. Synthesis of phenanthridinones from biaryl-2- oxamic acids via intramolecular decarboxylative cyclization

Scheme 21. Intramolecular Minisci acylation for the synthesis of azafluorenones

Scheme 22. Reaction of N-(p-methoxy aryl) proparynamides and α-ketoic acids towards azaspiro[4,5]trienones

Scheme 23. Synthesis of acylated indole[2,1-α]isoquinolines from 2,3-aryl-N-acryloyl indoles and α-keto acids

Scheme 24. Synthesis of carbamoylated benzimidazo[2,1-a]iso- quinolin-6(5H)-ones via radical cascade cyclization

Scheme 25. Cyclization of ortho-cyanoarylacrylamides with oxamic acids to access carbamoyl quinoline-2,4-diones

Scheme 26. Visible light-induced decarboxylative acylarylation of phenyl propiolates with α-keto acids catalyzed by hypervalent iodine

Scheme 27. Visible-light-induced decarboxylative coupling reactions for the synthesis of 4?aryl-2-quinolinones

Scheme 28. Photoredox-catalyzed decarboxylation of oxamic acids towards 3,4-dihydroquinolin-2?ones

Scheme 29. Visible-light-induced decarboxylative cyclization of 2-alkenylarylisocyanides with α?keto acids towards 2?acylindoles

Scheme 30. Visible-light-induced decarboxylative cyclization/hydrogenation to access phenanthridin-6-yl(aryl)methanol via an electron donor-acceptor complex

Scheme 31. Photoredox catalysis enables decarboxylative cyclization of hypervalent iodine(III) reagents and α-keto acids towards 2,5-disubstituted 1,3,4-oxadiazoles

Scheme 32. Photo-induced decarboxylative acylation/cycliza- tion of unactivated alkenes with α-keto acids

Scheme 33. Hydrogen radical-shuttle (HRS)-enabled photoredox synthesis of indanones via decarboxylative annulation

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