Alkylation of pyrimido[5′,4′:5,6]pyrido[3,2-b]indol-4-one derivatives

被引：1
|
作者：
Masterova, N. S. [1 ]
Alekseeva, L. M. [1 ]
Shashkov, A. S. [2 ]
Tafeenko, V. A. [3 ]
Ryabova, S. Yu. [1 ]
Granik, V. G. [1 ]
机构：
[1] State Res Ctr Antibiot, Moscow 117003, Russia
[2] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
[3] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2008年 / 57卷 / 08期
关键词：
11-benzyl-3,11-dihydro-4H-pyrimido[5 ',4 ':5,6]pyrido[3,2-b]indol-4-one; X-ray diffraction analysis; alkylation; 3-and 6-monoalkylpyrimido[5 ',4 ':5,6]pyrido[3,2-b]indol-4-ones; 3,6-dialkylpyrimido[5 ',4 ':5,6]pyrido[3,2-b]indol-4-ones; halides;
D O I：
10.1007/s11172-008-0234-1
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Alkylation of 11-benzyl-3,11-dihydro-4H-pyrimido[5',4':5,6]pyrido[3,2-b]indol-4-one with methyl iodide and methyl bromoacetate in DMF gave 3-alkylpyrimidopyridoindolones as the corresponding salts. The reaction in acetone in the presence of K2CO3 yielded 3,6-disubstitution products. Alkylation with DMF dimethyl acetal gave a mixture of the 3- and 6-alkylpyrimidopyridoindol-4-one bases. The structure of 4-oxo-4,6-dihydro-3H-pyrimido-[5',4':5,6]pyrido[3,2-b]indol-11-ium chloride (3b) was proved by X-ray diffraction analysis.
引用
收藏
页码：1765 / 1772
页数：8
相关论文
共 50 条
  • [1] Alkylation of pyrimido[5′,4′:5,6]pyrido[3,2-b]indol-4-one derivatives
    N. S. Masterova
    L. M. Alekseeva
    A. S. Shashkov
    V. A. Tafeenko
    S. Yu. Ryabova
    V. G. Granik
    [J]. Russian Chemical Bulletin, 2008, 57 : 1765 - 1772
  • [2] Synthesis of derivatives of the new heterocyclic system pyrimido[5',4':5,6]pyrido[3,2-b]indole
    Ryabova, S. Yu.
    Alekseeva, L. M.
    Masterova, N. S.
    Granik, V. G.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2007, 56 (08) : 1588 - 1594
  • [3] Synthesis of derivatives of the new heterocyclic system pyrimido[5′,4′:5,6]pyrido[3,2-b]indole
    S. Yu. Ryabova
    L. M. Alekseeva
    N. S. Masterova
    V. G. Granik
    [J]. Russian Chemical Bulletin, 2007, 56 : 1588 - 1594
  • [4] SYNTHESIS OF 3-AMINO-5H-PYRIMIDO[5,4-B]INDOL-4-ONE DERIVATIVES
    MONGE, A
    PALOP, JA
    PARRADO, P
    PEREZILZARBE, C
    FERNANDEZALVAREZ, E
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (02) : 437 - 439
  • [5] Synthesis and structure elucidation of new 3,5-dihydro-4H-pyrimido[5,4-b]indol-4-one derivatives
    Barone, Mariarita
    Catalfo, Alfio
    [J]. ARABIAN JOURNAL OF CHEMISTRY, 2017, 10 : S3444 - S3450
  • [6] Synthesis and antitumor evaluation of novel tetrahydrobenzo[4,5]thieno[3,2:5,6]pyrimido[1,2-b]isoquinoline derivatives
    Mahmoud, Mahmoud R.
    Abu El-Azm, Fatma S. M.
    Ismail, Mahmoud F.
    Hekal, Mohamed H.
    Ali, Yasmeen M.
    [J]. SYNTHETIC COMMUNICATIONS, 2018, 48 (04) : 428 - 438
  • [7] Synthesis of novel pyrido[3′,2′:5,6]thiopyrano[3,2-b]indol-5(6H)-ones and 6H-pyrido[3′,2′:5,6]thiopyrano[4,3-b]quinolines, two new heterocyclic ring systems
    Da Settimo, A
    Marini, AM
    Primofiore, G
    Da Settimo, F
    Salerno, S
    Simorini, F
    Pardi, G
    La Motta, C
    Bertini, D
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (05) : 1001 - 1006
  • [8] Synthesis and antimicrobial activities of pyrano[3,2-c]quinoline, pyrimido [5′,4′:5,6]pyrano[3,2-c]quinoline and [1,2,4]triazolo[2",3":1′,6′]pyrimido [5′,4′:5,6]pyrano[3,2-c]quinoline derivatives
    El Mariah, Fatma
    [J]. JOURNAL OF CHEMICAL RESEARCH, 2009, (09) : 588 - 592
  • [9] One-pot approach to construct benzo[4,5]thieno[3,2-b]indoles, pyrido [3′,2′:4,5]thieno[3,2-b]indoles and pyrazino[2′,3′:4,5]thieno[3,2-b] indoles based on the Fischer indole synthesis
    Irgashev, Roman A.
    Steparuk, Alexander S.
    Rusinov, Gennady L.
    [J]. TETRAHEDRON, 2020, 76 (52)
  • [10] INDOLE BETA-NUCLEOPHILIC SUBSTITUTION .3. SYNTHESIS OF 4 ISOMERIC PYRIDO[X',Y' - 5,6]OXEPINO[3,2-B]INDOLONES
    BEAL, MG
    ASHCROFT, WR
    COOPER, MM
    JOULE, JA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (02): : 435 - 439
12345