Title:
METHOD FOR SYNTHESIZING CHIRAL SPIRO-TETRAHYDROFURAN-PYRAZOLONE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2023/173651
Kind Code:
A1
Abstract:
Disclosed in the present invention is a method for synthesizing a chiral spiro-tetrahydrofuran-pyrazolone compound, specifically comprising: taking vinyl cyclic carbonate and α,β-unsaturated pyrazolone as reactants, Pd(PPh3)4 as a metal, and a chiral phosphorus ligand as a chiral ligand, and performing a reaction in an organic solvent to obtain a chiral spiro-tetrahydrofuran-pyrazolone compound. The method disclosed in the present invention is simple and easy to obtain raw materials, mild in reaction conditions, simple and convenient in post-treatment, wide in the range of applicable substrates, high in yield and high in enantioselectivity; the synthesized product can be used for synthesizing an intermediate of a drug.
Inventors:
WANG XINGWANG (CN)
LV HAOPENG (CN)
LV HAOPENG (CN)
Application Number:
PCT/CN2022/109311
Publication Date:
September 21, 2023
Filing Date:
July 31, 2022
Export Citation:
Assignee:
UNIV SOOCHOW (CN)
International Classes:
C07D491/107
Foreign References:
| CN114591344A | 2022-06-07 |
Other References:
MONDAL BUDDHADEB, MAITY RAJENDRA, PAN SUBHAS CHANDRA: "Highly Diastereo- and Enantioselective Synthesis of Spiro-tetrahydrofuran-pyrazolones via Organocatalytic Cascade Reaction between γ-Hydroxyenones and Unsaturated Pyrazolones", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 83, no. 15, 3 August 2018 (2018-08-03), pages 8645 - 8654, XP093092538, ISSN: 0022-3263, DOI: 10.1021/acs.joc.8b00781
BIMING MAO; HONGLEI LIU; ZHENGYANG YAN; YI XU; JIAQING XU; WEI WANG; YONGJUN WU; HONGCHAO GUO: "Palladium‐Catalyzed Asymmetric [4+2] Cycloaddition of 2‐Methylidenetrimethylene Carbonate with Alkenes: Access to Chiral Tetrahydropyran‐Fused Spirocyclic Scaffolds", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 59, no. 28, 11 May 2020 (2020-05-11), Hoboken, USA, pages 11316 - 11320, XP072093598, ISSN: 1433-7851, DOI: 10.1002/anie.202002765
HUIHUI ZHANG; XING GAO; FENG JIANG; WANGYU SHI; WEI WANG; YONGJUN WU; CHENG ZHANG; XUEYAN SHI; HONGCHAO GUO: "Palladium‐Catalyzed Asymmetric [3+2] Cycloaddition of Vinylethylene Carbonates with 2‐Arylidene‐1,3‐Indandiones: Synthesis of Tetrahydrofuran‐Fused Spirocyclic 1,3‐Indandiones", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2020, no. 30, 4 August 2020 (2020-08-04), DE , pages 4801 - 4804, XP072121748, ISSN: 1434-193X, DOI: 10.1002/ejoc.202000762
WU QIONG, MA CHUN, DU XI-HUA, CHEN YAN, CAI PEI-JUN: "Diversity-Oriented Synthesis of Spiropyrazolone-Based Tetrahydropyrroles via Three-Component 1,3-Dipolar Cycloadditions", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE., vol. 48, no. 04, STUTTGART, DE. , pages 595 - 605, XP093092542, ISSN: 0039-7881, DOI: 10.1055/s-0035-1560966
BIMING MAO; HONGLEI LIU; ZHENGYANG YAN; YI XU; JIAQING XU; WEI WANG; YONGJUN WU; HONGCHAO GUO: "Palladium‐Catalyzed Asymmetric [4+2] Cycloaddition of 2‐Methylidenetrimethylene Carbonate with Alkenes: Access to Chiral Tetrahydropyran‐Fused Spirocyclic Scaffolds", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 59, no. 28, 11 May 2020 (2020-05-11), Hoboken, USA, pages 11316 - 11320, XP072093598, ISSN: 1433-7851, DOI: 10.1002/anie.202002765
HUIHUI ZHANG; XING GAO; FENG JIANG; WANGYU SHI; WEI WANG; YONGJUN WU; CHENG ZHANG; XUEYAN SHI; HONGCHAO GUO: "Palladium‐Catalyzed Asymmetric [3+2] Cycloaddition of Vinylethylene Carbonates with 2‐Arylidene‐1,3‐Indandiones: Synthesis of Tetrahydrofuran‐Fused Spirocyclic 1,3‐Indandiones", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2020, no. 30, 4 August 2020 (2020-08-04), DE , pages 4801 - 4804, XP072121748, ISSN: 1434-193X, DOI: 10.1002/ejoc.202000762
WU QIONG, MA CHUN, DU XI-HUA, CHEN YAN, CAI PEI-JUN: "Diversity-Oriented Synthesis of Spiropyrazolone-Based Tetrahydropyrroles via Three-Component 1,3-Dipolar Cycloadditions", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE., vol. 48, no. 04, STUTTGART, DE. , pages 595 - 605, XP093092542, ISSN: 0039-7881, DOI: 10.1055/s-0035-1560966
Attorney, Agent or Firm:
SUZHOU CREATOR PATENT AND TRADEMARK AGENCY, LTD (CN)
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