Synthesis of cyclopropa[c]indeno[1,2-b]quinolines through a MCR/Staudinger/aza-Wittig sequence

被引:6
|
作者
Nie, Bing-Jie [1 ]
Wu, Li-Hui [1 ]
Hu, Ruo-Fei [1 ]
Sun, Yang [1 ]
Wu, Jing [1 ]
He, Ping [1 ]
Huang, Nian-Yu [2 ]
机构
[1] Hubei Univ Arts & Sci, Coll Chem Engn & Food Sci, Xiangyang 441053, Hubei, Peoples R China
[2] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Yichang, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
Cyclopropa[c]indeno[1; 2-b]quinolines; multicomponent reaction; spirocyclopropane; Staudinger; aza-Wittig reaction; HIGHLY STEREOSELECTIVE-SYNTHESIS; MULTICOMPONENT REACTIONS; ONE-POT; CYCLOPROPANES; CONSTRUCTION; DERIVATIVES; CHEMISTRY; BIOLOGY; DESIGN; ACIDS;
D O I
10.1080/00397911.2017.1328065
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Spirocyclopropanes were prepared from aromatic aldehydes, 1,3-indandione and acetophenones through a halogenation/S(N)2-displacement/Michael-initiated ring-closing sequence by a pyridinium-ylide-assisted multicomponent reaction, and their further use was also researched in the construction of cyclopropa[c]indeno[1,2-b]quinolines through subsequent Staudinger/aza-Wittig reactions.
引用
收藏
页码:1368 / 1374
页数:7
相关论文
共 50 条
  • [31] Unexpected synthesis of indolo[1,2-c]quinazolines by a sequential Ugi 4CC-Staudinger-aza-Wittig-nucleophilic addition reaction
    He, Ping
    Nie, Yi-Bo
    Wu, Jing
    Ding, Ming-Wu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (05) : 1429 - 1436
  • [32] Synthesis and characterization of indeno[1,2-b]fluorene-based low bandgap copolymers for photovoltaic cells
    Kim, Jinseck
    Kim, Sun Hee
    Jung, In Hwan
    Jeong, Eunjae
    Xia, Yangjun
    Cho, Shinuk
    Hwang, In-Wook
    Lee, Kwanghee
    Suh, Hongsuk
    Shim, Hong-Ku
    Woo, Han Young
    JOURNAL OF MATERIALS CHEMISTRY, 2010, 20 (08) : 1577 - 1586
  • [33] Synthesis of pseudopeptidic (S)-6-amino-5-oxo-1,4-diazepines and (S)-3-benzyl-2-oxo-1,4-benzodiazepines by an Ugi 4CC Staudinger/aza-Wittig sequence
    Lecinska, Paulina
    Corres, Nazaret
    Moreno, Daniel
    Garcia-Valverde, Maria
    Marcaccini, Stefano
    Torroba, Tomas
    TETRAHEDRON, 2010, 66 (34) : 6783 - 6788
  • [34] Multicomponent one-pot solvent-free synthesis of functionalized unsymmetrical dihydro-1H-indeno[1,2-b]pyridines
    Samai, Subhasis
    Nandi, Ganesh Chandra
    Kumar, Ram
    Singh, M. S.
    TETRAHEDRON LETTERS, 2009, 50 (50) : 7096 - 7098
  • [35] Multi-component one-pot synthesis of unsymmetrical dihydro-5H-indeno[1,2-b]quinolines as new pH indicators
    Shirini, Farhad
    Beigbaghlou, Somayyeh Sarvi
    Atghia, Seyyed Vahid
    Mousazadeh, Seyyed Ali-Reza
    DYES AND PIGMENTS, 2013, 97 (01) : 19 - 25
  • [36] Synthesis of tetracyclic azasugars fused benzo[e][1,3]thiazin-4-one by the tandem Staudinger/aza-Wittig/cyclization and their HIV-RT inhibitory activity
    Shao, Jie
    Zhu, Mo
    Gao, Ligang
    Chen, Hua
    Li, Xiaoliu
    CARBOHYDRATE RESEARCH, 2018, 456 : 45 - 52
  • [37] Organic synthesis in water: a green protocol for the synthesis of 2-(cyclohexylamino)-3-aryl- indeno[1,2-b]furan-4-ones
    Heravi, Majid M.
    Baghernejad, Bita
    Oskooie, Hossein A.
    MOLECULAR DIVERSITY, 2009, 13 (03) : 385 - 387
  • [38] One-pot synthesis of tetrahydro-pyrrolobenzodiazepines and tetrahydro-pyrrolobenzodiazepinones through sequential 1,3-dipolar cycloaddition/N-alkylation (N-acylation)/Staudinger/aza-Wittig reactions
    Ma, Xiaoming
    Zhang, Xiaofeng
    Awad, John Mark
    Xie, Guoshu
    Qiu, Weiqi
    Zhang, Wei
    GREEN CHEMISTRY, 2019, 21 (16) : 4489 - 4494
  • [39] Triflates Promoted One-Pot Synthesis of Functionalized Unsymmetrical New Dihydro-1h-Indeno[1,2-B]Pyridines Through Hantzsch Reaction under Ultrasonic Irradiation
    Turhan, Kadir
    Ozturkcan, S. Arda
    Turgut, Zuhal
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2012, 34 (01): : 94 - 101
  • [40] A New Four-Component Reaction for the Synthesis of Spiro[4H-indeno[1,2-b]pyridine-4,3′-[3H]indoles]
    Feiz, Afsaneh
    Shakibaei, Ghazaleh Imani
    Yasaei, Zahra
    Khavasi, Hamid Reza
    Bazgir, Ayoob
    HELVETICA CHIMICA ACTA, 2011, 94 (09) : 1628 - 1637