Diastereoselective Cascade Assembly of Functionalized Pyrano[3,4-c]pyrrole Derivatives

被引：21
|
作者：
Ievlev, Mikhail Yu. [1 ]
Ershov, Oleg V. [1 ]
Tafeenko, Viktor A. [2 ]
机构：
[1] Ulyanov Chuvash State Univ, Moskovsky Pr 15, Cheboksary 428015, Russia
[2] Moscow MV Lomonosov State Univ, Leninskie Gory 1, Moscow 119991, Russia
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 08期
基金：
俄罗斯基础研究基金会;
关键词：
DOMINO-SYNTHESIS; TETRACYANOETHYLENE; 4-OXOALKANE-1,1,2,2-TETRACARBONITRILES; DIARYLETHENE;
D O I：
10.1021/acs.orglett.6b00867
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel convenient approach for the synthesis of densely functionalized pyrano[3,4-c]pyrrole derivatives was developed. Cascade transformation of the simple adducts of tetracyanoethylene (TCNE) and ketones (4-oxoalkane-1,1,2,2-tetracarbonitriles) in the presence of aldehyde under the action of acetic acid led to the diastereoselective formation of targeted pyrano[3,4-c]pyrroles. The reaction pathway was thoroughly investigated, and proposed intermediates consistent with experiment. were shown to be
引用
收藏
页码：1940 / 1943
页数：4
相关论文
共 50 条
  • [31] A facile synthesis of 3,4-disubstituted isoxazole derivatives by regioselective cleavage of pyrano[3,4-c]isoxazoles with boron trihalide
    Kim, HJ
    Lee, YJ
    SYNTHETIC COMMUNICATIONS, 1998, 28 (19) : 3527 - 3537
  • [32] New synthesis of 6,8-diamino-substituted pyrano[3,4-c]pyridines from related pyrano[3,4-c]pyridin-6-one
    Paronikyan, Ervand G.
    Ayvazyan, Armen G.
    Mamyan, Suren S.
    Dashyan, Shushanik Sh.
    MENDELEEV COMMUNICATIONS, 2024, 34 (01) : 129 - 130
  • [33] Green synthesis of highly functionalized octahydropyrrolo[3,4-c]pyrrole derivatives using subcritical water, and their anti(myco)bacterial and antifungal activity
    Nural, Yahya
    Gemili, Muge
    Yabalak, Erdal
    De Coen, Laurens M.
    Ulger, Mahmut
    ARKIVOC, 2018, : 51 - 64
  • [34] Synthesis and properties of benzo[c]-, pyrrolo[3,4-c]-, and thieno[3,4-c]-pyrrole-4,6-dione copolymers
    Lu, Yong
    Lei, Yanlian
    Wu, Bo
    Xu, Xiaofeng
    Zhu, Furong
    Hu, Xiao
    Ong, Beng S.
    Ng, Siu Choon
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (04) : 2642 - 2650
  • [35] Cascade of the acylation/intramolecular oxo-Diels-Alder reaction for the diastereoselective synthesis of thienyl substituted hexahydropyrano [3,4-c]pyrrole-1,6-diones
    Zaytsev, Vladimir P.
    Surina, Nataliya S.
    Pokazeev, Kuzma M.
    Shelukho, Evgeniya R.
    Yakovleva, Elizaveta D.
    Nadirova, Maryana A.
    Novikov, Roman A.
    Khrustalev, Victor N.
    Zubkov, Fedor I.
    TETRAHEDRON LETTERS, 2023, 120
  • [36] TETRAOXO DERIVATIVES OF PERHYDROPYRROLO[3,4-C]PYRIDINE
    FERAPPI, M
    CAROTTI, A
    CASINI, G
    DELAURENTIS, N
    GIARDINA, D
    CINGOLANI, GM
    GAVUZZO, E
    MAZZA, F
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (02) : 439 - 446
  • [37] Synthesis of Furo[3,4-c]furanones via DDQ Treatment of Furo[3,4-c]pyranone Derivatives
    Meng, Tao
    Fuhrer, Cyril A.
    Haener, Robert
    SYNLETT, 2009, (12) : 1951 - 1954
  • [38] Novel benzopyrano[3,4-c]pyrrole derivatives as potent and selective dopamine D3 receptor antagonists
    Dubuffet, T
    Newman-Tancredi, A
    Cussac, D
    Audinot, V
    Loutz, A
    Millan, MJ
    Lavielle, G
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (14) : 2059 - 2064
  • [39] Synthesis of derivatives of pyrano[3,4-c][1,2,4]triazolo[4,3-a]pyridine and 8-(pyrazol-1-yl)pyrano[3,4-c]pyridine through pyridine ring rearrangement
    Paronikyan, Ervand G.
    Dashyan, Shushanik Sh.
    Minasyan, Nune S.
    Stepanyan, Grachya M.
    Ayvazyan, Armen G.
    Tamazyan, Rafael A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (12) : 1078 - 1086
  • [40] IN VITRO EVALUATION OF ANTITUBULIN ACTIVITY OF TETRAHYDROPYRROLO[3,4-c]PYRROLE-1,3-DIONE DERIVATIVES
    Zelazkova, Jana
    REVUE ROUMAINE DE CHIMIE, 2019, 64 (06) : 493 - 495
12345