α-酮酸的脱羧酰基化/环化反应研究进展

doi:10.6023/cjoc202205025

摘要/Abstract

α-酮酸的脱羧反应是得到酰基自由基的简便高效的方法, 而连续的自由基环化反应是合成环状结构, 特别是杂环结构的重要途径. 通过α-酮酸脱羧产生酰基自由基引发的自由基环化反应, 可以高效构建酰基化的吲哚酮、喹啉酮、菲啶、香豆素、色酮、苯并噻吩、吡咯[1,2-a]吲哚等结构. 介绍了α-酮酸脱羧产生酰基自由基而引发的自由基历程的酰基化/环化反应的最新进展.

关键词: α-酮酸, 环化反应, 自由基反应, 酰基化

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

引用此文

吴业春, 于金涛. α-酮酸的脱羧酰基化/环化反应研究进展[J]. 有机化学, 2022, 42(11): 3606-3619.

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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图/表 33

图式1. AgNO3催化N-芳基丙烯酰胺与α-酮酸合成酰基化吲哚酮

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

图式2. AgNO3催化肉桂酰胺与α-酮酸合成C-3酰基二氢喹啉酮

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

图式3. AgNO3催化α-酮酸与N-芳基肉桂酰胺合成C-3酰基化喹啉酮及二氢吲哚酮

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

图式4. 银催化2-异腈联苯与α-酮酸盐合成6-酰基菲啶

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

图式5. AgNO3促进炔酸酯与α-酮酸合成3-酰基香豆素

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

图式6. 炔酸酯与α-酮酸的5-外环化反应合成3-酰基香豆素

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

图式7. 银催化邻氰基丙烯酰胺与α-酮酸的反应合成酰基化的喹啉-2,4-二酮

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

图式8. AgNO3催化串联脱羧/氧化环化反应合成二氢黄酮

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

图式9. 2-炔基硫代苯甲醚与α-酮酸合成3-酰基苯并噻吩

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

图式10. 银催化邻羟基芳胺酮与α-酮酸合成3-酰基色满酮

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

图式11. 2-氰基-3-芳基丙烯酰胺与α-酮酸的脱羧环化反应

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

图式12. 银催化草氨酸与偕二氟烯烃合成3,4-二氢喹啉酮

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

图式13. 银催化草氨酸的脱羧自由基加成/环化反应合成喹啉-2-酮

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

图式14. 银催化N-芳基丙酰胺与α-酮酸合成螺[4,5]三烯酮反应

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

图式15. N-丙炔基吲哚与丙酮酸反应合成单酰化和二酰化吡咯[1,2-a]吲哚

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

图式16. 银催化脱羧酰胺基化反应合成酰胺化的异喹啉二酮和吲哚酮

Scheme 16. Silver-catalyzed decarboxylative aminoformylation towards azaheterocyclic acetamides

图式17. 银催化N-烯丙基吲哚与α-羰基酸合成吡咯[1,2-a]吲哚

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

图式18. 银催化亚烷基环丙烷的C—C-σ?键的酰基化/芳基化反应合成2-酰基-3,4二氢萘

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

图式19. 钯催化酮肟与草氨酸的脱羧邻位酰胺化反应

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

图式20. 联芳基-2-酰胺酸分子内脱羧合成菲咯烷酮

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

图式21. 分子内Minisci酰基化合成氮杂芴酮

Scheme 21. Intramolecular Minisci acylation for the synthesis of azafluorenones

图式22. N-(对甲氧基芳基)丙炔酰胺与α-酮酸合成氮杂螺[4,5]-三烯酮反应

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

图式23. 2,3-二芳基-N-丙烯酰基吲哚与α-酮酸合成酰基化吲哚[2,1-α]异喹啉

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

图式24. 自由基串联环化反应与合成氨甲酰化的苯并咪唑- [2,1-a]异喹啉-6(5H)-酮

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

图式25. 邻氰基-N-芳基丙烯酰胺与草氨酸的自由基环化反应合成氨甲酰基取代喹啉-2,4-二酮

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

图式26. 可见光促进高价碘催化丙酸苯酯与α-酮酸的脱羧酰基化反应

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

图式27. 可见光促进的脱羧偶联反应合成4-芳基-2-喹啉酮

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

图式28. 光催化草氨酸脱羧合成3,4-二氢喹啉-2(1H)-酮

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

图式29. 可见光促进2-烯基芳基异氰与α-酮酸的脱羧环化反应合成2-酰基吲哚

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

图式30. 可见光促进电子供体-受体复合物参与的脱羧环化/氢化反应合成(6-菲啶基)甲醇

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

图式31. 光催化高价碘试剂与α-酮酸的脱羧环化反应合成2,5-二取代1,3,4-噁二唑

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

图式32. 光促进非活化烯烃与α-酮酸的脱羧酰基化/环化反应

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

图式33. 氢自由基穿梭机促进的光催化脱羧环化合成茚满酮

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

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