SYNTHESIS OF 2,3-DIHYDRO-IMIDAZO[1,2-C]PYRIMIDO[5',4'-4,5]THIEN[2,3-E]PYRIMIDINES AND 2H-3,4-DIHYDRO-PYRIMIDO[1,2-C]PYRIMIDO[5',4'-4,5]THIENO[2,3-E]PYRIMIDINES

被引:0
|
作者
WAGNER, G [1 ]
VIEWEG, H [1 ]
LEISTNER, S [1 ]
机构
[1] UNIV LEIPZIG,FACHBEREICH BIOWISSENSCH,O-7010 LEIPZIG,GERMANY
来源
PHARMAZIE | 1993年 / 48卷 / 08期
关键词
D O I
暂无
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The reaction of dibenzoyldiacetonitrile with cyanothioacetamide gave 5-cyano-6-methyl-2-phenyl-pyri-mid-4(3H)-thione (4) in good yield. The title compounds were synthesized on two different routes. On one way, 3-amino-thieno[2,3-d]pyrimidine-2-carbonic acid alkylesters obtained from 4 were after acetylation of the amino group to 9 transformed by reaction of aminoethanol to the hydroxy ethylated pyrimidothienopyrimidone 10b. This compound after chlorination to 11 by reaction with 1,2-diaminoethan or 1,3-diaminopropan yielded the desired tetracyclic substances 12 and 13. On the other way, 3-aminothieno[2,3-d]pyrimidine-2-carboxamide 14 obtained from 4 gave via the pyrimidothienopyrimidone 15, the chloro compound 17 and the omega-hydroxyalkyl compounds 21 and 22 the title substances 23 and 24.
引用
下载
收藏
页码:588 / 591
页数:4
相关论文
共 50 条
  • [41] Reactions of uracils, 2.3.: Subsequent reactions of 7-ethoxypyrimido[4,5-d]pyrimidines:: Nucleophilic exchange, pyrimido[4,5:4′,5′]pyrimido[1,2-a]quinazolines, benzo[f]pyrimido[4,5:4′,5′] pyrimido[1,2-d][1,3,4]triazepine
    Wamhoff, H
    Muhr, J
    Horn, M
    Sohár, P
    Csámpai, A
    HETEROCYCLIC COMMUNICATIONS, 1999, 5 (04) : 365 - 376
  • [42] Synthesis and Antibacterial Activities of Novel 2,5-Diphenylindolo[2,3-e] Pyrazolo[1′,5′:3",4"]pyrimido[2",1"-c] [1,2,4]triazines
    Atta, Kamal F. M.
    Farahat, Omaima O. M.
    Ghobashy, Somaya M.
    Marei, Mohamed G.
    MOLECULES, 2011, 16 (12): : 10387 - 10408
  • [43] I2-DMSOmediatedtetra-functionalizationofenaminonesfortheconstructionofnovelfuro[2,3:4,5]pyrimido[1,2-b]indazoleskeletonsviainsitucaptureofketeniminecations
    You Zhou
    LiSheng Wang
    ShuangGui Lei
    BoCheng Tang
    ZhiCheng Yu
    Xing Li
    YanDong Wu
    KaiLu Zheng
    AnXin Wu
    Chinese Chemical Letters, 2025, 36 (01) : 306 - 311
  • [44] Synthesis and transformations of 2-amino-1-(4,5-dihydro-1H-imidazol-2-yl)benzimidazoles. A route to 2,3-dihydrobenzo[4,5]imidazo[1,2-c]imidazo[1,2-a][1,3,5]triazine ring system
    Saczewski, F
    Debowski, T
    Szmigiel, J
    HETEROCYCLES, 1998, 48 (09) : 1879 - 1885
  • [45] Synthesis and Biological Evaluation of Benzo [4,5]- and Naphtho[2′,1′:4,5]imidazo[1,2-c]pyrimidinone Derivatives
    Kamzeeva, Polina
    Dagaev, Nikolai
    Lizunova, Sofia
    Khodarovich, Yuri
    Sogomonyan, Anna
    Kolchanova, Anastasia
    Pokrovsky, Vadim
    Alferova, Vera
    Chistov, Alexey
    Eshtukov-Shcheglov, Artur
    Eshtukova-Shcheglova, Elizaveta
    Belyaev, Evgeny
    Skvortsov, Dmitry
    Varizhuk, Anna
    Aralov, Andrey
    BIOMOLECULES, 2023, 13 (11)
  • [46] SYNYHESIS AND COMPUTAIONAL STUDIES OF SOME PYRIMIDO[4\,5\:4,5]THIENO[2,3-d] PYRIMIDINE COMPOUNDS
    Mussa, Sunman M.
    Ashoor, Salem El-T.
    Albahi, Lamia A.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 25 (3-4) : 251 - 261
  • [47] Cycloalkano[1",2":4,5;4",3":4′,5′]bis(pyrrolo[2,3-c]pyrimido-[5,4-e]pyridazines):: synthesis, structure and mechanism of their formation
    Serduke, OV
    Gulevskaya, AV
    Pozharskii, AF
    Starikova, ZA
    Profatilova, IA
    TETRAHEDRON, 2006, 62 (04) : 652 - 661
  • [48] Synthesis of thieno[2′,3′:4,5]pyrimido[2,1-c][1,2,4]triazoles and pyrazolylthieno[2,3-d][4,5-d′]dipyrimidines
    Geies, AA
    JOURNAL OF CHEMICAL RESEARCH-S, 1998, (06): : 290 - +
  • [49] Novel syntheses of 5-aminothieno[2,3-c]pyridazine, pyrimido[4',5':4,5]thieno[2,3-c]pyridazine, pyridazino[4',3':4,5]thieno[3,2-d][1,2,3]triazine and phthalazine derivatives
    El-Gaby, MSA
    El-Dean, AMK
    Gaber, AEM
    Eyada, HA
    Al-Kamali, ASN
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (08) : 1181 - 1187
  • [50] SYNTHESES OF SUBSTITUTED PYRAZOLO[3,4-B]QUINOLINES, 3,4-DIHYDRO-4-OXOPYRIMIDO[4',5'-4,5]THEINO[2,3-B]QUINOLINE AND PYRIDO[1',2'-1,2]PYRIMIDO[4,5-B]QUINOLINE
    NEELIMA
    BHAT, B
    BHADURI, AP
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (03) : 925 - 928