Catalyst-free Tandem 1,3-Dipolar Cycloaddition/Aldol Condensation: Diastereoselective Construction of the Azatetraquinane Skeleton

被引：10
作者：
Zimnitskiy, Nikolay S. [1 ]
Denikaev, Andrey D. [1 ]
Barkov, Alexey Y. [1 ]
Kutyashev, Igor B. [1 ]
Korotaev, Vladislav Y. [1 ]
Sosnovskikh, Vyacheslav Y. [1 ]
机构：
[1] Ural Fed Univ, Inst Nat Sci & Math, Ekaterinburg 620000, Russia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 13期
基金：
俄罗斯基础研究基金会;
关键词：
STABILIZED AZOMETHINE YLIDES; STEREOSELECTIVE-SYNTHESIS; NATURAL-PRODUCTS; CAGE COMPOUNDS; REGIO; NINHYDRIN; MULTICOMPONENT; CRINIPELLIN; DERIVATIVES; CURCUMIN;
D O I：
10.1021/acs.joc.0c01127
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The one-pot regioselective and diastereoselective method for the synthesis of 5-(het)aroyl-7-(het)-arylhexahydrobenzo[4,5]pentaleno[1,6a-b](thia)pyrrolizine-6,12-diones from accessible 1,5-di(het)arylpent-4-ene-1,3-diones or curcuminoids in 38-98% yield was developed. This reaction proceeds as a sequence of 1,3-dipolar cycloaddition of azomethine ylide generated in situ from ninhydrin and (thia)proline at the C=C bond of corresponding enedione, followed by spontaneous intramolecular aldol condensation and leads to the formation of an azatetraquinane scaffold.
引用
收藏
页码：8683 / 8694
页数：12
相关论文
共 50 条
  • [31] Enantioselective Synthesis of the Chiral Pyrrolidine Fragment of Upadacitinib via Chiral Auxiliary Directed Diastereoselective 1,3-Dipolar Cycloaddition
    Sampath, Magesh
    Jayaraman, Sembian Ruso
    Eda, Vishnuvardhan Reddy
    Potham, Rajendar
    Budhdev, Rajeev Rehani
    Sen, Saikat
    Bandichhor, Rakeshwar
    Oruganti, Srinivas
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2022, 26 (06) : 1794 - 1802
  • [32] A highly regioselective tandem 1,3-dipolar cycloaddition of cyclopropene 1,1-diesters and nitrile oxides: synthesis of highly functionalized isoxazoles
    Chen, Shaojin
    Ren, Jun
    Wang, Zhongwen
    TETRAHEDRON, 2009, 65 (45) : 9146 - 9151
  • [33] Diastereoselective 1,3-dipolar intramolecular nitrone olefin cycloaddition (INOC) reaction of a sugar-derived allyl alcohol: Synthesis of functionalized aminocyclopentitols
    Rohokale, Rajendra
    CARBOHYDRATE RESEARCH, 2024, 543
  • [34] Racemic and diastereoselective construction of indole alkaloids under solvent- and catalyst-free microwave-assisted Pictet-Spengler condensation
    Jida, Mouhamad
    Soueidan, Olivier-Mohamad
    Deprez, Benoit
    Laconde, Guillaume
    Deprez-Poulain, Rebecca
    GREEN CHEMISTRY, 2012, 14 (04) : 909 - 911
  • [35] Diastereoselective Three-Component 1,3-Dipolar Cycloaddition to Access Functionalized β-Tetrahydrocarboline- and Tetrahydroisoquinoline-Fused Spirooxindoles
    Wang, Yongchao
    Chen, Yu
    Duan, Shengli
    Cao, Yiyang
    Sun, Wenjin
    Zhang, Mei
    Zhao, Delin
    Hu, Donghua
    Dong, Jianwei
    MOLECULES, 2024, 29 (08):
  • [36] Highly Diastereoselective 1,3-Dipolar Cycloaddition of a D-Galactose-Derived Nitrone with Dimethyl Maleate: Synthesis of Polyhydroxylated Perhydroazaazulenes
    Bande, Omprakash P.
    Jadhav, Vrushali H.
    Puranik, Vedavati G.
    Dhavale, Dilip D.
    SYNLETT, 2009, (12) : 1959 - 1963
  • [37] Straightforward and Highly Diastereoselective Synthesis of a New Set of Functionalized Dispiropyrrolidines Involving Multicomponent 1,3-Dipolar Cycloaddition with Azomethine Ylides
    Boudriga, Sarra
    Elmhawech, Besma
    Moheddine, Askri
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (06) : 1748 - 1756
  • [38] Microwave-assisted synthesis of pyrrolidinyl-spirooxindoles via tandem 1,3-dipolar cycloaddition and oxidative dehydrogenation
    Tan, Hong-bo
    Xiang, Yu-heng
    Huang, Jing-wen
    Ren, Si-ying
    Lin, Chang-qiu
    Xu, Zhi-gang
    Tang, Dian-yong
    Chen, Zhong-zhu
    TETRAHEDRON, 2025, 169
  • [39] Synthesis of Pyrrole via a Silver-Catalyzed 1,3-Dipolar Cycloaddition/Oxidative Dehydrogenative Aromatization Tandem Reaction
    Liu, Yan
    Hu, Huayou
    Wang, Xiang
    Zhi, Sanjun
    Kan, Yuhe
    Wang, Chao
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08) : 4194 - 4202
  • [40] Copper-Catalyzed Regio- and Diastereoselective 1,3-Dipolar Cycloaddition Reactions of Glycine Imino Esters with 1-Propene-1,3-sultone
    Furuya, Shohei
    Kato, Shuma
    Kanemoto, Kazuya
    Fukuzawa, Shin-ichi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (28) : 4561 - 4565
12345