Diastereoselective Synthesis of Highly Functionalized γ-Lactams via Ugi Reaction/Michael Addition

被引：0
作者：
Vidal, Herika D. A. [1 ]
Nunes, Paulo S. G. [1 ]
Martinez, Alice K. A. [1 ]
Januario, Marcelo A. P. [1 ]
Santiago, Pedro H. O. [2 ]
Ellena, Javier [2 ]
Correa, Arlene G. [1 ]
机构：
[1] Univ Fed Sao Carlos, Ctr Excellence Res Sustainable Chem, Dept Chem, BR-13565 Sao Carlos, Brazil
[2] Univ Sao Paulo, SAo Carlos Inst Phys, BR-13563 Sao Carlos, SP, Brazil
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2025年 / 20卷 / 01期
基金：
巴西圣保罗研究基金会;
关键词：
gamma-lactams; 3-cyano-2-pyrrolidinones; Ugi reaction; Michael addition; One-pot reactions; SMALL-MOLECULE; HETEROCYCLES; CYCLIZATION; PART;
D O I：
10.1002/asia.202400917
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The gamma-lactam ring is a prominent feature in medicinal chemistry, and its synthesis has garnered significant interest due to its valuable properties. Among the gamma-lactams, 2-oxopyrrolidine-3-carbonitrile derivatives stand out as versatile synthons that can be readily transformed into a variety of other functional groups. In this work, we successfully synthesized highly functionalized 3-cyano-2-pyrrolidinones with moderate to good overall yields using the Ugi reaction followed by intramolecular Michael addition. The process demonstrated excellent diastereoselectivity and showed good tolerance to a range of isonitriles and carbonyl compounds.
引用
收藏
页数：6
相关论文
共 66 条
  • [1] Ugi Multicomponent Reaction Based Synthesis of Medium-Sized Rings
    Abdelraheem, Eman M. M.
    Madhavachary, Rudrakshula
    Rossetti, Arianna
    Kurpiewska, Katarzyna
    Kalinowska-Tluscik, Justyna
    Shaabani, Shabnam
    Domling, Alexander
    [J]. ORGANIC LETTERS, 2017, 19 (22) : 6176 - 6179
  • [2] Recent Advances in the Synthesis of α-Alkylidene-Substituted δ-Lactones, γ-Lactams and δ-Lactams
    Albrecht, Anna
    Albrecht, Lukasz
    Janecki, Tomasz
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (15) : 2747 - 2766
  • [3] The Ugi Reaction of Cyanoacetic Acid as a Route to Tetramic Acid Derivatives
    Alvarez-Rodriguez, Nancy V.
    Dos Santos, Aurelie
    El Kaim, Laurent
    Gamez-Montano, Rocio
    [J]. SYNLETT, 2015, 26 (16) : 2253 - 2256
  • [4] Regio- and chemo-selective cyclization of allenic-Ugi products for the synthesis of 3-pyrroline skeletons
    Amiri, Kamran
    Khosravi, Hormoz
    Balalaie, Saeed
    Golmohammadia, Farhad
    Anware, Muhammad U.
    Al-Harrasi, Ahmed
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (39) : 8858 - 8870
  • [5] REDUCTION OF NITRILES TO PRIMARY AMINES WITH LITHIUM ALUMINUM HYDRIDE
    AMUNDSEN, LH
    NELSON, LS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (01) : 242 - 244
  • [6] [Anonymous], 2024, CrysAlis PRO
  • [7] Synthesis of seven-membered nitrogen heterocycles through the Ugi multicomponent reaction
    Banfi, Luca
    Basso, Andrea
    Lambruschini, Chiara
    Moni, Lisa
    Riva, Renata
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (04) : 382 - 408
  • [8] Post-Ugi Cyclization for the Construction of Diverse Heterocyclic Compounds: Recent Updates
    Bariwal, Jitender
    Kaur, Rupinder
    Voskressensky, Leonid G.
    Van der Eycken, Erik V.
    [J]. FRONTIERS IN CHEMISTRY, 2018, 6
  • [9] Palladium Catalysis Enabled Sequential C(sp3)-H/C-C Activation: Access to Vinyl γ-Lactams
    Barman, Madhab
    Mishra, Manmath
    Mandal, Santu
    Punniyamurthy, Tharmalingam
    [J]. ORGANIC LETTERS, 2024, 26 (18) : 3722 - 3726
  • [10] Enzymatic assembly of the salinosporamide γ-lactam-β-lactone anticancer warhead
    Bauman, Katherine D.
    Shende, Vikram V.
    Chen, Percival Yang-Ting
    Trivella, Daniela B. B.
    Gulder, Tobias A. M.
    Vellalath, Sreekumar
    Romo, Daniel
    Moore, Bradley S.
    [J]. NATURE CHEMICAL BIOLOGY, 2022, 18 (05) : 538 - +
1234567