Access and Modulation of Substituted Pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones

被引：0
|
作者：
Ejjoummany, Abdelaziz [1 ,2 ]
Elie, Jonathan [1 ]
El Hakmaoui, Ahmed [2 ]
Akssira, Mohamed [2 ]
Routier, Sylvain [1 ]
Buron, Frederic [1 ]
机构：
[1] Univ Orleans, Inst Chim Organ & Analyt, UMR CNRS 7311, BP 6759, F-45067 Orleans 2, France
[2] Univ Hassan II Casablanca, Fac Sci & Tech, BP 146, Mohammadia 28800, Morocco
来源：
MOLECULES | 2023年 / 28卷 / 15期
关键词：
pyrrolo[3; 4-c] pyrazole; cross-coupling; fused [5; 5] ring systems; PYRAZOLE DERIVATIVES; DESIGN;
D O I：
10.3390/molecules28155811
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The first access to polyfunctionnalized pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-dione derivatives is reported. The series were generated from diethyl acetylenedicarboxylate and arylhydrazines, which afforded the key intermediates bearing two functional positions. The annellation to generate the maleimide moiety of the bicycle was studied. Moreover, an efficient palladium-catalyzed C-C and C-N bond formation via Suzuki-Miyaura or Buchwald-Hartwig coupling reactions in C-6 position was investigated from 6-chloropyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones. This method provides novel access to various 1,6 di-substituted pyrrolo[3,4-c] pyrazole-4,6-(2H,5H)-diones.
引用
收藏
页数：18
相关论文
共 50 条
  • [21] Synthesis of pyrrolo [3,4-c][1]benzazepine-4,10(2H,5H)-dione, a model system useful for the design of 11-oxosibiromycinone analogues
    DiSanto, R
    Costi, R
    Massa, S
    Artico, M
    SYNTHETIC COMMUNICATIONS, 1996, 26 (10) : 1839 - 1847
  • [22] Synthesis of Pyrrolo[3,4-c][1]benzazepine-4,10(2H,5H)- @dione, a Model System Useful for the Design of 11-Oxosibiromycinone Analogues
    Synth Commun, 10 (1839):
  • [23] Synthesis of C-Glycosyl Pyrrolo[3,4-c]carbazole-1,3(2H,6H)-diones as a Scaffold for Check Point Kinase 1 Inhibitors
    Ichikawa, Satoshi
    Tatebayashi, Nana
    Matsuda, Akira
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (23): : 12065 - 12075
  • [24] 2,5-Dihexyl-3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
    Sevincek, Resul
    Celik, Secil
    Aygun, Muhittin
    Alp, Serap
    Isik, Samil
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1546 - U351
  • [25] 1, 3-Dipolar cycloaddition reactions: Synthesis of 5-benzyl-1-(2′,4′-dibromophenyl)-3-(4″-substituted phenyl)-3a,4,6,6a-tetrahydro-1H, 5H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives
    MANPREET KAUR
    BALDEV SINGH
    BALJIT SINGH
    Journal of Chemical Sciences, 2013, 125 : 1529 - 1534
  • [26] 1, 3-Dipolar cycloaddition reactions: Synthesis of 5-benzyl-1-(2′,4′-dibromophenyl)-3-(4"-substituted phenyl)-3a,4,6,6a-tetrahydro-1H, 5H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives
    Kaur, Manpreet
    Singh, Baldev
    Singh, Baljit
    JOURNAL OF CHEMICAL SCIENCES, 2013, 125 (06) : 1529 - 1534
  • [27] SYNTHESIS AND PHARMACOLOGICAL PROPERTIES OF NEW DERIVATIVES OF 4-ALKOXY-6-METHYL-1H-PYRROLO[3,4-c]PYRIDINE-1,3(2H)-DIONES
    Sladowska, Helena
    Sabiniarz, Aleksandra
    Sapa, Jacek
    Filipek, Barbara
    ACTA POLONIAE PHARMACEUTICA, 2009, 66 (01): : 57 - 63
  • [28] Synthesis and biological activity of some new pyrazoline and pyrrolo[3,4-c]pyrazole-4,6-dione derivatives: Reaction of nitrilimines with some dipolarophiles
    Abunada, Nada M.
    Hassaneen, Hamdi M.
    Kandile, Nadia G.
    Miqdad, Omar A.
    MOLECULES, 2008, 13 (04) : 1011 - 1024
  • [29] Preparation of 7-arylmethyl-1H-pyrrolo[3,4-c]pyridine-1,3-(2H)-diones and α-aryl-3-hydroxy-5-pyridylacetonitriles using arynic methodology
    Wang, AL
    Tandel, S
    Zhang, HM
    Huang, YW
    Holdeman, TC
    Biehl, ER
    TETRAHEDRON, 1998, 54 (14) : 3391 - 3400
  • [30] NEW SYNTHESIS OF 2H-PYRROLO[3,4-C]QUINOLINES
    FRITZ, H
    SCHENK, S
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1975, (02): : 255 - 265
12345