Annulations involving 1-indanones to access fused- and spiro frameworks

被引:9
|
作者
Das, Suven [1 ]
Dutta, Arpita [2 ]
机构
[1] Rishi Bankim Chandra Coll Women, Dept Chem, Naihati 743165, India
[2] Rishi Bankim Chandra Evening Coll, Dept Chem, Naihati 743165, India
关键词
EXOCYCLIC ALPHA; BETA-UNSATURATED KETONES; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; PHOTOPHYSICAL PROPERTIES; CONSTRUCTION; REARRANGEMENT; EFFICIENT; YLIDES; TANDEM; DERIVATIVES;
D O I
10.1039/d2ra06635a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Indanones are prominent motifs found in number of natural products and pharmaceuticals. Particularly, 1-indanones occupy important niche in chemical landscape due to their easy accessibility and versatile reactivity. In the past few years, significant advancement has been achieved regarding cyclization of 1-indanone core. The present review focuses on recent (2016-2022) annulations involving 1-indanones for the construction of fused- and spirocyclic frameworks. In this context, new strategies for synthesis of various carbocyclic as well as heterocyclic skeletons are demonstrated. Mechanistic aspects of representative reactions are illustrated for better understanding of reaction pathways. A large number of transformations described in this review offer stereoselective formation of desired polycyclic compounds. Importantly, several reactions provide biologically relevant compounds and natural products, such as, plecarpenene/plecarpenone, swinhoeisterol A, cephanolides A-D, diptoindonesin G and atlanticone C.
引用
收藏
页码:33365 / 33402
页数:38
相关论文
共 32 条
  • [1] A two-step access to fused-/spiro-polycyclic frameworks via double Heck cascade and acid-driven processes
    Goel, Komal
    Satyanarayana, Gedu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 34 (6919-6925) : 6919 - 6925
  • [2] Annulations involving p-benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules
    Das, Suven
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (18) : 8243 - 8276
  • [3] Metal-free radical cascade cyclization/haloazidation of enynones to access functionalized 1-indanones
    Yan, Hua-Feng
    Zou, Xiao
    Wang, Jian-Qiang
    Guo, Cheng
    Zuo, Hang-Dong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (05) : 1067 - 1072
  • [4] Recent applications of 1,3-indanedione in organic transformations for the construction of fused- and spiro scaffolds
    Das, Suven
    TETRAHEDRON, 2022, 122
  • [5] Annulations involving 2-arylidene-1,3-indanediones: stereoselective synthesis of spiro- and fused scaffolds
    Das, Suven
    NEW JOURNAL OF CHEMISTRY, 2020, 44 (40) : 17148 - 17176
  • [6] Easy access to some chiral 2- or 3-substituted 1-indanones and 3,4-dihydrocoumarins
    Poras, Herve
    Stephan, Elie
    Pourcelot, Guy
    Cresson, Pierre
    Chemistry and Industry (London), 1993, (06): : 206 - 207
  • [7] EASY ACCESS TO SOME CHIRAL 2-SUBSTITUTED OR 3-SUBSTITUTED 1-INDANONES AND 3,4-DIHYDROCOUMARINS
    PORAS, H
    STEPHAN, E
    POURCELOT, G
    CRESSON, P
    CHEMISTRY & INDUSTRY, 1993, (06) : 206 - 207
  • [8] An Intramolecular Umpolung Cascade Kukhtin-Ramirez Reaction/ Michael Addition-Initiated Cyclization: Stereoselective Synthesis of Tetrasubstituted Fused 1-Indanones
    Sar, Suman
    Ghorai, Prasanta
    ORGANIC LETTERS, 2023, 25 (11) : 1946 - 1951
  • [9] Highly diastereoselective one-pot synthesis of spiro{cyclopenta[a]indene-2,2′-indene}diones from 1-indanones and aromatic aldehydes
    Camps, P
    Domingo, LR
    Formosa, X
    Galdeano, C
    González, D
    Muñoz-Torrero, D
    Segalés, S
    Font-Bardia, M
    Solans, X
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09): : 3464 - 3471
  • [10] Access to fused pyrroles via the reaction of spiro-dienyl ethers with amines involving a chemoselective skeletal rearrangement
    Zhang, Xiaoyu
    Huang, Li
    Peng, Hui
    Ji, Fanghua
    Li, Xuehui
    Yin, Biaolin
    TETRAHEDRON, 2014, 70 (34) : 5242 - 5248