Copper-Catalyzed Synthesis of Substituted 2,4-Diamino-1,3,5-triazines from 1,1-Dibromoalkenes and Biguanides

被引:31
|
作者
Zhang, Chen [1 ]
Ban, Meng-Tao [1 ]
Zhu, Kai [2 ]
Zhang, Li-Yu [3 ]
Luo, Zhen-Yu [1 ]
Guo, Shun-Na [1 ]
Cui, Dong-Mei [2 ]
Zhang, Yu [3 ]
机构
[1] Zhejiang Univ, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
[3] Jiamusi Univ, Sch Pharmaceut Sci, Jiamusi 154007, Peoples R China
关键词
MICROWAVE-ASSISTED SYNTHESIS; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; TRIAZINE DENDRIMERS; ARYL ALDEHYDES; S-TRIAZINES; PALLADIUM; 1,1-DIBROMO-1-ALKENES; DERIVATIVES; 1,3,5-TRIAZINES;
D O I
10.1021/acs.orglett.7b01608
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient copper-catalyzed synthesis of substituted 2,4-diamino-1,3,5-triazines from 1,1-dibromoalkenes and biguanides under mild conditions has been developed. The reaction occurred in moderate to good yields and tolerated alkyl-, heterocyclic-, or aryl-substituted 1,1-dibromoalkenes containing functionalities such as nitriles, ethers, and halogens. Monosubstituted to tetrasubstituted biguanidines also afforded the desired products.
引用
收藏
页码:3947 / 3949
页数:3
相关论文
共 50 条
  • [41] PROIZVODNYE 2,4-DIAMINO-1,3,5-TRIAZILALKILKARBONOVYKH KISLOT .1.
    SOKOLOVSKAYA, SV
    SOKOLOVA, VN
    MAGIDSON, OY
    ZHURNAL OBSHCHEI KHIMII, 1953, 23 (03): : 467 - 472
  • [42] Trisubstituted 1,3,5-triazines. 3. Synthesis of substituted 2,4,6-tris(hydroxyiminomethyl)-1,3,5-triazines
    Sbastin, A.V.
    Godovikova, T.I.
    Korsunskii, B.L.
    Chemistry of Heterocyclic Compounds, 1999, 35 (01): : 72 - 74
  • [43] Synthesis, structure, and dynamic behavior in solution of arylamino-1,3,5-triazines - 1. Unsymmetrically substituted arylamino-1,3,5-triazines
    Belyakov, PA
    Shastin, AV
    Strelenko, YA
    RUSSIAN CHEMICAL BULLETIN, 2005, 54 (10) : 2441 - 2451
  • [44] Trisubstituted 1,3,5-triazines. 3. Synthesis of substituted 2,4,6-tris(hydroxyiminomethyl)-1,3,5-triazines
    Shastin, AV
    Godovikova, TI
    Korsunsky, BL
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1999, (01): : 76 - 78
  • [45] Acid-Base Properties and Complex Formation of 2,4-Diamino-6-(Carbamoylmethylsulphinyl)-1,3,5-Triazines
    Salnikov, Yu., I
    Boos, G. A.
    Fattakhov, S. G.
    Shulaeva, M. M.
    Chmutova, G. A.
    Khusainova, A. R.
    Neklyudov, V. V.
    UCHENYE ZAPISKI KAZANSKOGO UNIVERSITETA-SERIYA ESTESTVENNYE NAUKI, 2011, 153 (03): : 48 - 60
  • [46] A novel straightforward synthesis of 2,4,6-triaryl-1,3,5-triazines via copper-catalyzed cyclization of N-benzylbenzamidines
    Debnath, Pradip
    Majumdar, K. C.
    TETRAHEDRON LETTERS, 2014, 55 (51) : 6976 - 6978
  • [47] ON 1,3,5-TRIAZINES .2. SYNTHESIS OF 2,4-DITHIO-3,5-DIARYL-6-PHENYLIMINO-HEXAHYDRO-1,3,5-TRIAZINES AND 2,6-DITHIO-3,5-DIARYL-4-PHENYLIMINO-HEXAHYDRO-1,3,5-TRIAZINES
    PATHE, PP
    AMBEKAR, MW
    NIMDEOKAR, NM
    PARANJPE, MG
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1982, 59 (05) : 670 - 672
  • [48] Domino synthesis of 1,3-diynes from 1,1-dibromoalkenes: a Pd-catalyzed copper-free coupling method
    Rao, Maddali L. N.
    Dasgupta, Priyabrata
    Ramakrishna, Boddu S.
    Murty, Venneti N.
    TETRAHEDRON LETTERS, 2014, 55 (25) : 3529 - 3533
  • [49] SYNTHESIS OF 1,3,5-TRIAZINES FROM AMINO ACID DERIVATIVES
    KUWANO, E
    TANIGUCHI, E
    MAEKAWA, K
    AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1971, 35 (10): : 1572 - +
  • [50] Dichloromethane as C1 Building Block: Synthesis of 2,4-Disubstitued 1,3,5-Triazines via Copper-Catalyzed Aerobic C-H/C-Cl Cleavage
    Yan, Yizhe
    Cui, Chang
    Wang, Jianyong
    Li, Shaoqing
    Liu, Yanqi
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) : 1166 - 1170