Synthesis of pyrimido[4,5-b]indoles and benzo[4,5]furo[2,3-d]pyrimidines via palladium-catalyzed intramolecular arylation

被引：42
|
作者：
Zhang, YM [1 ]
Razler, T [1 ]
Jackson, PF [1 ]
机构：
[1] Johnson & Johnson Pharmaceut Res & Dev, LLC, Raritan, NJ 08869 USA
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 46期
关键词：
D O I：
10.1016/S0040-4039(02)02036-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Various pyrimido[4,5-b]indoles and benzo[4,5]furo[2,3-d]pyrimidines were synthesized via a palladium-catalyzed intramolecular arylation of pyrimidine substrates. Thus, 4-aryloxy- or 4-anilino-5-iodopyrimidines were treated with Pd(OAc)(2)(PPh3)(2) and base in DMF to give the regioselective cyclized heterocycles. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8235 / 8239
页数：5
相关论文
共 50 条
  • [31] Synthesis of functional 2-substituted 4-phenyl-9H-pyrimido[4,5-b]indoles
    V. P. Borovik
    O. P. Shkurko
    Russian Chemical Bulletin, 2002, 51 : 2129 - 2133
  • [32] Synthesis of functional 2-substituted 4-phenyl-9H-pyrimido[4,5-b]indoles
    Borovik, VP
    Shkurko, OP
    RUSSIAN CHEMICAL BULLETIN, 2002, 51 (11) : 2129 - 2133
  • [33] 5-ACETYL-6-AMINO-4-METHYLTHIO-2-PHENYLPYRIMIDINE AND ITS USE IN THE SYNTHESIS OF FUNCTIONALIZED PYRIDO[2,3-D]PYRIMIDINES AND PYRIMIDO[4,5-D]PYRIMIDINES
    KOMKOV, AV
    SAKHAROV, AM
    BOGDANOV, VS
    DOROKHOV, VA
    RUSSIAN CHEMICAL BULLETIN, 1995, 44 (07) : 1278 - 1282
  • [34] Practical Way to Imidazo[4,5-b] and [4,5-c]Pyridine-2-ones via Cascade Ureidation/Palladium-Catalyzed Cyclization
    Lach, Franck
    Koza, Patrice
    ACS COMBINATORIAL SCIENCE, 2012, 14 (09) : 491 - 495
  • [35] SYNTHESIS OF SOME(1,2,3)THIADIAZOLO)5,4-D)PYRIMIDINES + PYRIMIDO)4,5-B))1,4)THIAZINES
    TAYLOR, EC
    GARCIA, EE
    JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (08): : 2121 - &
  • [36] Green Method for the Synthesis of Benzo[f]pyrimido[4,5-b]quinoline Derivatives Catalyzed by Iodine in Aqueous Media
    Wang, Xiang-Shan
    Li, Qing
    Wu, Jian-Rong
    Zhang, Mei-Mei
    SYNTHETIC COMMUNICATIONS, 2009, 39 (17) : 3069 - 3080
  • [37] An efficient one-pot three-component synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water
    Verma, Girijesh K.
    Raghuvanshi, Keshav
    Kumar, Ram
    Singh, Maya Shankar
    TETRAHEDRON LETTERS, 2012, 53 (04) : 399 - 402
  • [38] General Approach To Construct Azepino[2,3-b:4,5-b′]diindoles, Azocino[2,3-b:4,5-b′]diindoles, and Azonino[2,3-b:4,5-b′]diindoles via Rh(II)-Catalyzed Reactions of 3-Diazoindolin-2-imines with 3-(Bromoalkyl)indoles
    Sheng, Guorong
    Li, Zhenmin
    Mao, Jianming
    Lu, Ping
    Wang, Yanguang
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (15): : 9561 - 9569
  • [39] 2,4-DIAMINOTHIENO [2,3-D] PYRIMIDINES AS ANTIFOLATES AND ANTIMALARIALS .2. SYNTHESIS OF 2,4-DIAMINOPYRIDO [4',3' - 4,5] THIENO [2,3-D] PYRIMIDINES AND 2,4-DIAMINO-8H-THIOPYRANO [4',3' - 4,5] THIENO [2,3-D] PYRIMIDINES
    CHAYKOVSKY, M
    LIN, M
    ROSOWSKY, A
    MODEST, EJ
    JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (03) : 188 - 191
  • [40] Three-component, one-pot synthesis of pyrimido[4,5-b]-quinoline and pyrido[2,3-d]pyrimidine derivatives
    Hassan, N. A.
    Hegab, M. I.
    Hashem, A. I.
    Abdel-Motti, F. M.
    Hebah, S. H. A.
    Abdel-Megeid, F. M. E.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (04) : 775 - 782
12345