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过渡金属催化合成异喹啉研究

杨定乔 蒙玲

杨定乔, 蒙玲. 过渡金属催化合成异喹啉研究[J]. 华南师范大学学报(自然科学版), 2013, 45(4).
引用本文: 杨定乔, 蒙玲. 过渡金属催化合成异喹啉研究[J]. 华南师范大学学报(自然科学版), 2013, 45(4).
PROGRESS IN TRANSITION-METAL CATALYZED SYNTHESIS OF ISOQUINOLINES11[J]. Journal of South China normal University (Natural Science Edition), 2013, 45(4).
Citation: PROGRESS IN TRANSITION-METAL CATALYZED SYNTHESIS OF ISOQUINOLINES11[J]. Journal of South China normal University (Natural Science Edition), 2013, 45(4).

过渡金属催化合成异喹啉研究

基金项目: 

铂催化不对称开环反应的研究

详细信息
    通讯作者:

    杨定乔

  • 中图分类号: O621.3

PROGRESS IN TRANSITION-METAL CATALYZED SYNTHESIS OF ISOQUINOLINES11

Funds: 

Studies of Pt-catalyzed asymmetric ring opening reactions

  • 摘要: 综述了近年来过渡金属催化合成异喹啉的研究进展,包括过渡金属钯、银、铜、铱、钌催化等,并对部分催化反应的机理进行了讨论.
  • [1]BENTLEY K W.The Isoquinoline alkaloids[M]. Amsterdam: Harwood academic publishers, 1998
    [2]MARTINE C D, ALAIN C, DANIELE C, et al.Diphenyl quinolines and isoquinolines: synthesis and primary biological evaluation[J].Bioorg Med Chem,2000,8(11):2629-2641
    [3]YANG Y Y, SHOU W G, CHEN Z B, et al.A tandem approach to isoquinolines from 2-azido-3-arylacrylates and α-diazocarbonyl compounds[J].J Org Chem,2008,73(10):3928-3930
    [4]PANDY G, BALAKRISHNAN M.Suzuki cross-coupling/reductive debenzyloxycarbonylation sequence for the syntheses of [c]annulated isoquinolines: application for the syntheses of pancratistatin-like isoquinolines[J].J Org Chem,2008,73(20):8128-8131
    [5]ISHIKAWA T, SHIMOOKA K, NARIOKA T, et al.Anomalous substituent effects in the Bischler?Napieralski reaction of 2-aryl aromatic formamides[J].J Org Chem,2000,65(26):9143-9151
    [6]SOTOMAYOR N, DOMINGUEZ E.Bischler?Napieralski cyclization?N/C-alkylation sequences for the construction of isoquinoline alkaloidsSynthesis of protoberberines and penzo[c]phenanthridines via C-2’-functionalized 3-arylisoquinolines[J].. J Org Chem,1996,61(12):4062-4072
    [7]YOUN S W.Development of the Pictet?Spengler reaction catalyzed by AuCl3/AgOTf[J].J Org Chem,2006,71(6):2521-2523
    [8]CHRZANOWSKA M, ROZWADOWSKA M D.Asymmetric synthesis of isoquinoline alkaloids[J].Chem Rev,2004,104(7):3341-3370
    [9]BOUDOU M, EENDERS D.Asymmetric synthesis of tetrahydropalmatine via tandem 1,2-addition/cyclization[J].J Org Chem,2005,70(23):9486-9494
    [10]WALKER E R, LEUNG S Y, BARRETT A G M.Studies towards the total synthesis of Sch 56036; isoquinolinone synthesis and the synthesis of phenanthrenes[J].Tetrahedron Lett,2005,46(38):6537-6540
    [11]ROESCH K R, LAROCK R C.Synthesis of isoquinolines and pyridines via Palladium-catalyzed iminoannulation of internal acetylenes[J].J Org Chem,1998,63(1):5306-5307
    [12]GIRLING I R, WIDDOMSON D A.Cyclopalladated imines in synthesis 2: a new synthesis of isoquinolines[J].Tetrahedron Lett,1982,23(41):4281-4284
    [13]MAASSARANI F, PFEFFER M, LEBORGNE G.Control of the reactivity of cyclopalladated complexes for the synthesis of heterocyclic compounds[J].J Chem Soc Chem Commun,1987,(8):565-567
    [14]WU G, GEIB S J, RHEINGOLD A L, HECK R F.Isoquinolinium salt syntheses from cyclopalladated benzaldimines and alkynes[J].J Org Chem,1988,53(14):3238-3241
    [15]ROESCH K R, LAROCK R C.Synthesis of isoquinolines and pyridines by the Palladium- and Copper-catalyzed coupling and cyclization of terminal acetylenes[J].Org Lett,1999,1(4):553-556
    [16]ROESCH K R, ZHANG H, LAROCK R C.Synthesis of isoquinolines and pyridines by the Palladium-catalyzed iminoannulation of internal alkynes[J].J Org Chem,2001,66(24):8042-
    [17]DAI G, LAROCK R C.Synthesis of 3,4-disubstituted isoquinolines via Palladium-catalyzed cross-coupling of o-(1-Alkynyl)benzaldimines and organic halides[J].Org Lett,2001,3(25):4035-4038
    [18]DAI G, LAROCK R C.Synthesis of 3-substituted 4-aroylisoquinolines via Pd-catalyzed carbonylative cyclization of o-(1-alkynyl)benzaldimines[J].Org Lett,2002,4(2):193-196
    [19]HUANG Q H, LAROCK R C.Synthesis of 4-(1-Alkenyl)isoquinolines by Palladium(II)-catalyzedcyclization/olefina
    [20]tion[J].J Org Chem, 2003, 68(3): 980-988
    [21]KONNO T, CHAE J, MIYABE T, et al.Regioselective one-step synthesis of 4-fluoro-alkylatedisoquinolines via carbopalladation reaction of fluorine-containing alkynes[J].J Org Chem,2005,70(24):10172-10174
    [22]FLORENTINO L, AZNAER F, VALDES C.Synthesis of polysubstituted isoquinolines through cross-coupling reactions with r-alkoxytosylhydrazones[J].Org Lett,2012,14(9):2323-2325
    [23]YANG D Q, BURUGUPALLI S, DANIEL D, et al.Microwave-assisted one-pot synthesis of isoquinolines, furopyridines, and thienopyridines by Palladium-catalyzed sequential coupling imination annulation of 2-bromoarylaldehydes with terminal acetylenes and ammonium acetate[J].J Org Chem,2012,77(9):4466-4472
    [24]GAO K, WU J.Synthesis of functionalized 1,2-dihydroisoquinolines via multicomponent one-pot reaction of 2-alkynylbenzaldehyde, amine, zinc, and allylic bromide or benzyl bromide[J].J Org Chem,2007,72(22):8611-8613
    [25]WANG B, LU B, JIANG Y W, et al.Assembly of isoquinolines via CuI-catalyzed coupling of β-keto esters and 2-halobenzylamines[J].Org Lett,2008,10(13):2761-2763
    [26]YU X X, WU J.Synthesis of functionalized isoquinolines via sequential cyclization/cross-coupling reactions[J].J Comb Chem,2009,11(5):895-899
    [27]DING Q P, WU J.Lewis acid- and organocatalyst-cocatalyzed multicomponent reactions of 2-alkynylbenzaldehydes, amines, and ketones[J].Org Lett,2007,9(24):4959-4962
    [28]NIU Y N, YAN Y Z, GAO G L, et al.Synthesis of isoquinoline derivatives via Ag-catalyzed cyclization of 2-alkynyl benzyl azides[J].J Org Chem,2009,74(7):2893-2896
    [29]YU X X, WU J.Synthesis of 1-(1H-indol-3-yl)-1,2-dihydroisoquinolines via AgOTf-catalyzed three component reactions of 2-alkynylbenzaldehydes, amines, and indoles[J].J Comb Chem,2010,12(2):238-244
    [30]REDDY M V R, RAO M R, RHODES D, et al.Lamellarin α 20-Sulfate, an inhibitor of HIV-1 integrase active against HIV-1 virus in cell culture[J].J Med Chem,1999,42(11):1901-1907
    [31]AUBRY A, PAN X S, FISHER L M, et al.Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity[J].Antimicrob Agents Chemother,2004,48(4):1281-1288
    [32]BAILLY C.Lamellarins, from A to Z: A family of anticancer marine pyrrole alkaloids[J].Curr Med Chem,2004,4(4):363-378
    [33]CHEN Z Y, WU J.Efficient generation of biologically active H-pyrazolo[5,1- a]isoquinolines via multicomponent reaction[J].Org Lett,2010,12(21):4856-4859
    [34]ZHENG D Q, LI S Y, WU J.An unexpected silver triflate catalyzed reaction of 2-alkynylbenzaldehyde with 2-isocyanoacetate[J].Org Lett,2012,14(11):2655-2657
    [35]LIM S G, LEE J H, MOON C W, et al.Rh(I)-catalyzed direct ortho-alkenylation of aromatic ketimines with alkynes and its application to the synthesis of isoquinoline derivatives[J].Org Lett,2003,5(15):2759-2761
    [36]GUIMOND N, FAGNOU K.Isoquinoline synthesis via rhodium-catalyzed oxidative cross-coupling/cyclization of aryl aldimines and alkynes[J].J Am Chem Soc,2009,131(34):12050-12051
    [37]TOO P C, WANG Y F, CHIBA S.Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone o-acyloxime derivatives and internal alkynes[J].Org Lett,2010,12(24):5688-5691
    [38]TOO P C, CHUA S H, WONG S H, et al.Synthesis of azaheterocycles from aryl ketone o-acetyl oximes and internal alkynes by Cu - Rh bimetallic relay catalysts[J].J Org Chem,2011,76(15):6159-6168
    [39]WEI X H, ZHAO M, DU Z Y, et al.Synthesis of 1-aminoisoquinolines via Rh(III)-catalyzed oxidative coupling[J].Org Lett,2011,13(17):4636-4639
    [40]ZHENG L Y, JU J, BIN Y H, et al.Synthesis of isoquinolines and heterocycle-fused pyridines via three-component cascade reaction of arylk etones, hydroxylamine, and alkynes[J].J Org Chem,2012,77(13):5794-5800
    [41]KISHOR P, JEGANMOHAN M.Highly regio- and stereoselective ruthenium(II)-catalyzed direct ortho-alkenylation of aromatic and heteroaromatic aldehydes with activated alkenes under open atmosphere[J].Org Lett,2012,14(4):1134-1137
    [42]KISHOR P, JEGANMOHAN M.Ruthenium-catalyzed ortho-alkenylation of aromatic ketones with alkenes by C–H bond activation[J].Org Lett,2011,13(23):6144-6147
    [43]CHINNAGOLLA R K, PIMPARKAR S, JEGANMOHAN M.Ruthenium-catalyzed highly regioselective cyclization of ketoximes with alkynes by C- H bond activation: a practical route to synthesize substituted isoquinolines[J].Org Lett,2012,14(12):3032-3035
    [44]KORNHAA? C, LI J, ACKERANN L.Cationic Ruthenium catalysts for alkyne annulations with oximes by C?H/N?O functionalizations[J].J Org Chem,2012,77(20):9190-9198
    [45]KORIVI R P, CHENG C H.Highly efficient synthesis of isoquinolines via Nickel-catalyzed annulation of 2-iodobenzaldimines with alkynes: evidence for dual pathways of alkyne insertion[J].Org Lett,2005,7(23):5179-5182
    [46]OKAMOTO N, TAKEDA K, YANADA R.Platinum-catalyzed, one-pot tandem synthesis of indoles and isoquinolines via sequential rearrangement of amides and aminocyclization[J].J Org Chem,2010,75(22):7615-7625

    [1]BENTLEY K W.The Isoquinoline alkaloids[M]. Amsterdam: Harwood academic publishers, 1998
    [2]MARTINE C D, ALAIN C, DANIELE C, et al.Diphenyl quinolines and isoquinolines: synthesis and primary biological evaluation[J].Bioorg Med Chem,2000,8(11):2629-2641
    [3]YANG Y Y, SHOU W G, CHEN Z B, et al.A tandem approach to isoquinolines from 2-azido-3-arylacrylates and α-diazocarbonyl compounds[J].J Org Chem,2008,73(10):3928-3930
    [4]PANDY G, BALAKRISHNAN M.Suzuki cross-coupling/reductive debenzyloxycarbonylation sequence for the syntheses of [c]annulated isoquinolines: application for the syntheses of pancratistatin-like isoquinolines[J].J Org Chem,2008,73(20):8128-8131
    [5]ISHIKAWA T, SHIMOOKA K, NARIOKA T, et al.Anomalous substituent effects in the Bischler?Napieralski reaction of 2-aryl aromatic formamides[J].J Org Chem,2000,65(26):9143-9151
    [6]SOTOMAYOR N, DOMINGUEZ E.Bischler?Napieralski cyclization?N/C-alkylation sequences for the construction of isoquinoline alkaloidsSynthesis of protoberberines and penzo[c]phenanthridines via C-2’-functionalized 3-arylisoquinolines[J].. J Org Chem,1996,61(12):4062-4072
    [7]YOUN S W.Development of the Pictet?Spengler reaction catalyzed by AuCl3/AgOTf[J].J Org Chem,2006,71(6):2521-2523
    [8]CHRZANOWSKA M, ROZWADOWSKA M D.Asymmetric synthesis of isoquinoline alkaloids[J].Chem Rev,2004,104(7):3341-3370
    [9]BOUDOU M, EENDERS D.Asymmetric synthesis of tetrahydropalmatine via tandem 1,2-addition/cyclization[J].J Org Chem,2005,70(23):9486-9494
    [10]WALKER E R, LEUNG S Y, BARRETT A G M.Studies towards the total synthesis of Sch 56036; isoquinolinone synthesis and the synthesis of phenanthrenes[J].Tetrahedron Lett,2005,46(38):6537-6540
    [11]ROESCH K R, LAROCK R C.Synthesis of isoquinolines and pyridines via Palladium-catalyzed iminoannulation of internal acetylenes[J].J Org Chem,1998,63(1):5306-5307
    [12]GIRLING I R, WIDDOMSON D A.Cyclopalladated imines in synthesis 2: a new synthesis of isoquinolines[J].Tetrahedron Lett,1982,23(41):4281-4284
    [13]MAASSARANI F, PFEFFER M, LEBORGNE G.Control of the reactivity of cyclopalladated complexes for the synthesis of heterocyclic compounds[J].J Chem Soc Chem Commun,1987,(8):565-567
    [14]WU G, GEIB S J, RHEINGOLD A L, HECK R F.Isoquinolinium salt syntheses from cyclopalladated benzaldimines and alkynes[J].J Org Chem,1988,53(14):3238-3241
    [15]ROESCH K R, LAROCK R C.Synthesis of isoquinolines and pyridines by the Palladium- and Copper-catalyzed coupling and cyclization of terminal acetylenes[J].Org Lett,1999,1(4):553-556
    [16]ROESCH K R, ZHANG H, LAROCK R C.Synthesis of isoquinolines and pyridines by the Palladium-catalyzed iminoannulation of internal alkynes[J].J Org Chem,2001,66(24):8042-
    [17]DAI G, LAROCK R C.Synthesis of 3,4-disubstituted isoquinolines via Palladium-catalyzed cross-coupling of o-(1-Alkynyl)benzaldimines and organic halides[J].Org Lett,2001,3(25):4035-4038
    [18]DAI G, LAROCK R C.Synthesis of 3-substituted 4-aroylisoquinolines via Pd-catalyzed carbonylative cyclization of o-(1-alkynyl)benzaldimines[J].Org Lett,2002,4(2):193-196
    [19]HUANG Q H, LAROCK R C.Synthesis of 4-(1-Alkenyl)isoquinolines by Palladium(II)-catalyzedcyclization/olefina
    [20]tion[J].J Org Chem, 2003, 68(3): 980-988
    [21]KONNO T, CHAE J, MIYABE T, et al.Regioselective one-step synthesis of 4-fluoro-alkylatedisoquinolines via carbopalladation reaction of fluorine-containing alkynes[J].J Org Chem,2005,70(24):10172-10174
    [22]FLORENTINO L, AZNAER F, VALDES C.Synthesis of polysubstituted isoquinolines through cross-coupling reactions with r-alkoxytosylhydrazones[J].Org Lett,2012,14(9):2323-2325
    [23]YANG D Q, BURUGUPALLI S, DANIEL D, et al.Microwave-assisted one-pot synthesis of isoquinolines, furopyridines, and thienopyridines by Palladium-catalyzed sequential coupling imination annulation of 2-bromoarylaldehydes with terminal acetylenes and ammonium acetate[J].J Org Chem,2012,77(9):4466-4472
    [24]GAO K, WU J.Synthesis of functionalized 1,2-dihydroisoquinolines via multicomponent one-pot reaction of 2-alkynylbenzaldehyde, amine, zinc, and allylic bromide or benzyl bromide[J].J Org Chem,2007,72(22):8611-8613
    [25]WANG B, LU B, JIANG Y W, et al.Assembly of isoquinolines via CuI-catalyzed coupling of β-keto esters and 2-halobenzylamines[J].Org Lett,2008,10(13):2761-2763
    [26]YU X X, WU J.Synthesis of functionalized isoquinolines via sequential cyclization/cross-coupling reactions[J].J Comb Chem,2009,11(5):895-899
    [27]DING Q P, WU J.Lewis acid- and organocatalyst-cocatalyzed multicomponent reactions of 2-alkynylbenzaldehydes, amines, and ketones[J].Org Lett,2007,9(24):4959-4962
    [28]NIU Y N, YAN Y Z, GAO G L, et al.Synthesis of isoquinoline derivatives via Ag-catalyzed cyclization of 2-alkynyl benzyl azides[J].J Org Chem,2009,74(7):2893-2896
    [29]YU X X, WU J.Synthesis of 1-(1H-indol-3-yl)-1,2-dihydroisoquinolines via AgOTf-catalyzed three component reactions of 2-alkynylbenzaldehydes, amines, and indoles[J].J Comb Chem,2010,12(2):238-244
    [30]REDDY M V R, RAO M R, RHODES D, et al.Lamellarin α 20-Sulfate, an inhibitor of HIV-1 integrase active against HIV-1 virus in cell culture[J].J Med Chem,1999,42(11):1901-1907
    [31]AUBRY A, PAN X S, FISHER L M, et al.Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity[J].Antimicrob Agents Chemother,2004,48(4):1281-1288
    [32]BAILLY C.Lamellarins, from A to Z: A family of anticancer marine pyrrole alkaloids[J].Curr Med Chem,2004,4(4):363-378
    [33]CHEN Z Y, WU J.Efficient generation of biologically active H-pyrazolo[5,1- a]isoquinolines via multicomponent reaction[J].Org Lett,2010,12(21):4856-4859
    [34]ZHENG D Q, LI S Y, WU J.An unexpected silver triflate catalyzed reaction of 2-alkynylbenzaldehyde with 2-isocyanoacetate[J].Org Lett,2012,14(11):2655-2657
    [35]LIM S G, LEE J H, MOON C W, et al.Rh(I)-catalyzed direct ortho-alkenylation of aromatic ketimines with alkynes and its application to the synthesis of isoquinoline derivatives[J].Org Lett,2003,5(15):2759-2761
    [36]GUIMOND N, FAGNOU K.Isoquinoline synthesis via rhodium-catalyzed oxidative cross-coupling/cyclization of aryl aldimines and alkynes[J].J Am Chem Soc,2009,131(34):12050-12051
    [37]TOO P C, WANG Y F, CHIBA S.Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone o-acyloxime derivatives and internal alkynes[J].Org Lett,2010,12(24):5688-5691
    [38]TOO P C, CHUA S H, WONG S H, et al.Synthesis of azaheterocycles from aryl ketone o-acetyl oximes and internal alkynes by Cu - Rh bimetallic relay catalysts[J].J Org Chem,2011,76(15):6159-6168
    [39]WEI X H, ZHAO M, DU Z Y, et al.Synthesis of 1-aminoisoquinolines via Rh(III)-catalyzed oxidative coupling[J].Org Lett,2011,13(17):4636-4639
    [40]ZHENG L Y, JU J, BIN Y H, et al.Synthesis of isoquinolines and heterocycle-fused pyridines via three-component cascade reaction of arylk etones, hydroxylamine, and alkynes[J].J Org Chem,2012,77(13):5794-5800
    [41]KISHOR P, JEGANMOHAN M.Highly regio- and stereoselective ruthenium(II)-catalyzed direct ortho-alkenylation of aromatic and heteroaromatic aldehydes with activated alkenes under open atmosphere[J].Org Lett,2012,14(4):1134-1137
    [42]KISHOR P, JEGANMOHAN M.Ruthenium-catalyzed ortho-alkenylation of aromatic ketones with alkenes by C–H bond activation[J].Org Lett,2011,13(23):6144-6147
    [43]CHINNAGOLLA R K, PIMPARKAR S, JEGANMOHAN M.Ruthenium-catalyzed highly regioselective cyclization of ketoximes with alkynes by C- H bond activation: a practical route to synthesize substituted isoquinolines[J].Org Lett,2012,14(12):3032-3035
    [44]KORNHAA? C, LI J, ACKERANN L.Cationic Ruthenium catalysts for alkyne annulations with oximes by C?H/N?O functionalizations[J].J Org Chem,2012,77(20):9190-9198
    [45]KORIVI R P, CHENG C H.Highly efficient synthesis of isoquinolines via Nickel-catalyzed annulation of 2-iodobenzaldimines with alkynes: evidence for dual pathways of alkyne insertion[J].Org Lett,2005,7(23):5179-5182
    [46]OKAMOTO N, TAKEDA K, YANADA R.Platinum-catalyzed, one-pot tandem synthesis of indoles and isoquinolines via sequential rearrangement of amides and aminocyclization[J].J Org Chem,2010,75(22):7615-7625
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出版历程
  • 收稿日期:  2013-05-26
  • 修回日期:  2013-04-22
  • 刊出日期:  2013-07-25

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