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Progress in Chemistry 2020, Vol. 32 Issue (11): 1710-1728 DOI: 10.7536/PC200601 Previous Articles   Next Articles

Application of Pyrazolone Compounds in Catalytic Asymmetric Reactions

Li Luyao1, Xu Xinyao1, Zhu Bo1,**(), Xu Xinyao1,**()   

  1. 1. School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China
  • Received: Online: Published:
  • Contact: Zhu Bo, Xu Xinyao
  • Supported by:
    the National Natural Science Foundation of China(81903465); the National Natural Science Foundation of China(U1804283)
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Pyrazolin-5-one compounds play an important role in bioactive compounds and have attracted extensive attention. Pyrazolin-5-one and its common derivatives have many reaction sites and can participate in a variety of asymmetric reactions, such as asymmetric addition reactions, asymmetric annulation reactions and other asymmetric reactions. In this context, we summarize the recent progress in asymmetric reactions of pyrazolin-5-one and its common derivatives. The main reaction types involving the pyrazolin-5-one compounds are classified, and their main reaction sites are expounded. Finally, the challenges and development of pyrazolone derivatives are summarized, and the future development direction is prospected.

Contents

1 Introduction

2 The synthesis of pyrazolin-5-one derivatives

3 Asymmetric addition reactions

3.1 Asymmetric Michael addition

3.2 Asymmetric Mannich reaction

3.3 Other asymmetric addition reaction

4 Asymmetric annulation reactions

5 Other asymmetric reactions

6 Conclusion and outlook

Key words: pyrazolin-5-one, asymmetric catalysis, addition reaction, annulation reaction
Scheme 1 Biologically active pyrazolone derivatives
Scheme 2 Reaction sites of pyrazolin-5-one derivatives
Scheme 3 The synthesis of pyrazolin-5-one derivatives[9,10,11]
Scheme 4 Asymmetric Michael addition of nitroalkenes and 1[12]
Scheme 5 Asymmertic Michael addition of different acceptors with 1 [13,14]
Scheme 6 Asymmetric Michael addition of 2-enoylpyridines or arylomethylidenemalonates with 1[15,16]
Scheme 7 Aza-Michael Addition of 1 to α,β-unsaturated ketones[17]
Scheme 8 Asymmetric Michael addition of nitroolefins and 2[18]
Scheme 9 Asymmetric Michael addition involving 2[19,20]
Scheme 10 Asymmmetric Michael addition of 2 to maleimides[21]
Scheme 11 Asymmmetric Michael addition of 2 with p-benzoquinones[22]
Scheme 12 Conjugate addition of 2 to the o-QMs[23]
Scheme 13 Asymmetric Michael addition of 2 to β-trifluoromethyl-α,β-unsaturated ketones[24]
Scheme 14 Asymmetric Michael addition of 2 to α,β-unsaturated p-nitrophenyl[9]
Scheme 15 Asymmetric Michael reaction of azlactones to 3[25]
Scheme 16 Asymmetric Michael reaction of nitroolefins to 4[26]
Scheme 17 Asymmetric Michael reaction of 3 with azomethine ylide[27]
Scheme 18 Asymmmetric Mannich reaction of 1 to isatin-derived N-Boc ketimines[28]
Scheme 19 Asymmetric synthesis of amino-bis-pyrazolone derivatives[29]
Scheme 20 Asymmetric Mannich reaction of 2 with isatin-derived ketimines[30]
Scheme 21 Asymmetric Mannich reactions between 3-fluorooxindoles and 5[31]
Scheme 22 Asymmetric Mannich reactions between 5 and β-ketoacids[32]
Scheme 23 Enantioselective aminoalkylation of 1[33]
Scheme 24 Other nucleophilic additions involving 1[34]
Scheme 25 Asymmetric α-amination of 1 or 2 with azodicarboxylates[35,36,37]
Scheme 26 Highly enantioselective regiodivergent addition of alkoxyallenes to 2[38]
Scheme 27 Asymmetric addition of 2 to allenamides[39]
Scheme 28 Asymmetric addition between TMSCN and 5[11]
Scheme 29 Asymmetric addition between enol ethers and 5[40]
Scheme 30 Enantioselective Aldol reaction of allyl ketones and 3-Acetylcoumarins to 6[41,42]
Scheme 31 Double Michael addition of 1 to aldehydes and possible reaction pathway[43,44]
Scheme 32 Multicomponent enantioselective [3+2] annulation reactions of 1[45]
Scheme 33 Four component [5+1+1+1] annulation reactions of 1[46]
Scheme 34 Asymmetric [4+1] annulation reactions between α,β-unsaturated keto esters, nitrosobenzenes and 1[47]
Scheme 35 One pot sequential multistep reaction involving 1[48,49]
Scheme 36 Asymmetric synergistic catalytic reactions involving 1 or 2[50,51,52]
Scheme 37 NHC-Catalyzed annulation betwwen enals and 1[53]
Scheme 38 Asymmetric annulation between enynones and1[54]
Scheme 39 Asymmetric cascade [5+1] double Michael additions between 1 and dienones[55]
Scheme 40 Phosphine-catalyzed [4+1] asymmetric annulation between 1 and 2-(acetoxymethyl)buta-2,3-dienoates[56]
Scheme 41 Asymmmetric annulation of(E)-5-nitro-6-arylhex-5-en-2-ones and 1[57]
Scheme 42 Asymmmetric [3+3] annulation of β,γ-unsaturated α-ketoesters and 1[58]
Scheme 43 Allenylic cycloaddition of allenyl acetates and 1[59]
Scheme 44 Rhodium-catalyzed asymmetric synthesis of spiropyrazolones by[60]
Scheme 45 Asymmetric [4+1] annulation of ortho-quinomethanes with 2[61]
Scheme 46 One pot sequential multistep annulation involoving 3[62,63]
Scheme 47 Annulation between ethyl acetoacetates,(E)-β-nitrostyrenes and 3[64]
Scheme 48 Annulation between aldehydes, nitrostyrenes and 3[65]
Scheme 49 Annulation between 3, enolizable aldehydes and enalsaldehydes[66]
Scheme 50 Asymmetric [3+2] annulation between 3, α-isothiocyanato imide and esters[67]
Scheme 51 Asymmetric [4+2] annulation between 3 and α,β-unsaturated ketones[68]
Scheme 52 Asymmetric [2+n] annulation involving 3[68,69,70,71,72,73,74,75,76,77]
Scheme 53 Asymmetric [3+2] annulation between 2-(1-methyl-2-oxoindolin-3-yl)malononitriles and 3[78]
Scheme 54 Asymmetric [3+2] annulation between MBH carbonates or 2,3-dienoate and 3[79,80]
Scheme 55 Asymmetric [4+2] annulation between 3 and α-chloroaldehydes[81]
Scheme 56 Asymmetric [4+2] annulation between 3 and arylacetic acid anhydride[82,83]
Scheme 57 Asymmetric [4+2] annulation between allenoates or allene ketones and 3[84]
Scheme 58 Asymmetric [3+3] annulation reaction between 4 and enals[85,86,87]
Scheme 59 Asymmetric [3+3] annulation reaction between 4 and(E)-2-nitroallylic acetates[88]
Scheme 60 Enantioselective [3+3] annulation reaction of MBH carbonates with 4[89]
Scheme 61 [1+2+3] multicomponent annulation reaction between malononitriles, benzaldehydes and 4[90]
Scheme 62 Enantioselective annulation reaction of β,γ-unsaturated-α-ketoesters with 4[91]
Scheme 63 Enantioselective annulation of 4 with alkyne [92]
Scheme 64 Asymmetric Michael-Aldol cyclization of β,γ-unsaturated α-ketoesters and 4[93]
Scheme 65 Asymmetric [3+2] cyclization of 4-isothiocyanato pyrazolones and isatin-derived ketimines[94]
Scheme 66 Asymmetric [4+2] cyclization of α,β,γ,δ-unsaturated pyrazolones and aldehydes[95]
Scheme 67 One pot sequential multistep reaction involving 1[96,97,98,99]
Scheme 68 Asymmetric fluorination/chlorination/hydroxylation of 2[100,101,102]
Scheme 69 Asymmetric allylation of 2[103,104]
Scheme 70 Enantioselective direct α-arylation of 2[105]
Scheme 71 Cross-dehydrogenative coupling between 1 and cyclopentenedione[106]
Scheme 72 Asymmetric sulfenylation of 2[107]
Scheme 73 Asymmetric reaction of 2 with isatin-derived nitroolefins[108]
Scheme 74 Asymmetric Friedel-Crafts reaction between 5 and β-Ketoacids[109]
Scheme 75 Asymmetric Friedel-Crafts reaction between 5 and hydroxyindoles[110]
Scheme 76 Asymmetric alkynylation of 6[111]
Scheme 77 Catalytic asymmetric Huisgen alkyne-azide cycloaddition of bisalkynes[112]
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