A one-pot construction of acridones by rhodium catalyzed reaction of N-phenyl-2-(1-sulfonyl-1H-1,2,3-triazol-4-yl)aniline

被引:10
作者
Xu, Hua-Dong [1 ]
Pan, Ying-Peng [1 ]
Ren, Xin-Tao [1 ]
Zhang, Ping [1 ]
Shen, Mei-Hua [1 ]
机构
[1] Changzhou Univ, Sch Pharmaceut Engn & Life Sci, Changzhou 213164, Jiangsu, Peoples R China
关键词
Acridone; N-Sulfonyl 1,2,3-trizaole; Rhodium carbene; Cyclization; Aza-vinyl metal carbene; N-SULFONYL 1,2,3-TRIAZOLES; DIVERGENT SYNTHESIS; 3+2 CYCLOADDITION; TERMINAL ALKYNES; SINGLET OXYGEN; N-SULFONYL-1,2,3-TRIAZOLES; 2H-AZIRINES; ALKALOIDS; TRANSANNULATION; ANNULATION;
D O I
10.1016/j.tetlet.2015.10.059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot synthesis of N-alkyl acridone via rhodium catalyzed decomposition of N-phenyl-2-(1-sulfonyl-1H-1,2,3-triazol-4-yl)aniline and subsequent oxidative C-C bond fragmentation has been developed. 14 examples are presented and the yields range from 30% to 80%. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6734 / 6737
页数:4
相关论文
共 36 条
  • [1] Allen CFH, 1939, ORG SYNTH, V19, P6
  • [2] A practical regiospecific approach towards acronycine and related alkaloids
    Anand, RC
    Selvapalam, N
    [J]. CHEMICAL COMMUNICATIONS, 1996, (02) : 199 - 200
  • [3] Recent Advances in Transition-Metal-Catalyzed Denitrogenative Transformations of 1,2,3-Triazoles and Related Compounds
    Anbarasan, Pazhamalai
    Yadagiri, Dongari
    Rajasekar, Shanmugam
    [J]. SYNTHESIS-STUTTGART, 2014, 46 (22): : 3004 - 3023
  • [4] SINGLET OXYGEN REACTION .4. PHOTOOXYGENATION OF ENAMINES INVOLVING A 2-STEP CLEAVAGE OF 1,2-DIOXETANE INTERMEDIATE
    ANDO, W
    SAIKI, T
    MIGITA, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (17) : 5028 - 5029
  • [5] Acridine and acridone derivatives, anticancer properties and synthetic methods: Where are we now?
    Belmont, Philippe
    Bosson, Johann
    Godet, Thomas
    Tiano, Martin
    [J]. ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2007, 7 (02) : 139 - 169
  • [6] Acridone Alkaloids from Glycosmis chlorosperma as DYRK1A Inhibitors
    Beniddir, Mehdi A.
    Le Borgne, Erell
    Iorga, Bogdan I.
    Loaec, Nadege
    Lozach, Olivier
    Meijer, Laurent
    Awang, Khalijah
    Litaudon, Marc
    [J]. JOURNAL OF NATURAL PRODUCTS, 2014, 77 (05): : 1117 - 1122
  • [7] Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles
    Davies, Huw M. L.
    Alford, Joshua S.
    [J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (15) : 5151 - 5162
  • [8] Rhodium(II)-catalyzed transannulation of 1-sulfonyl-1,2,3-triazoles with 2H-azirines: a new method to dihydropyrazines
    Ding, Haixin
    Hong, Sanguo
    Zhang, Ning
    [J]. TETRAHEDRON LETTERS, 2015, 56 (03) : 507 - 510
  • [9] REACTION OF SINGLET OXYGEN WITH OLEFINS - QUESTION OF MECHANISM
    FRIMER, AA
    [J]. CHEMICAL REVIEWS, 1979, 79 (05) : 359 - 387
  • [10] Synthesis of β-Amino-α,β-unsaturated Ketone Derivatives via Sequential Rhodium-Catalyzed Sulfur Ylide Formation/Rearrangement
    He, Jun
    Man, Zengming
    Shi, Yinping
    Li, Chuan-Ying
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09) : 4816 - 4823