Serendipitous Formation of 2H-Pyrazolo[3,4-d]pyridazin-7(6H)-ones from 3-Arylsydnones

被引：5

作者：

Kumbar, Mahadev N. ^{[1
]}

Shaikh, Saba Kauser J. ^{[1
]}

Kamble, Ravindra R. ^{[1
]}

Bayannavar, Praveen K. ^{[1
]}

Kamble, Atulkumar A. ^{[1
]}

Hunnur, Raveendra K. ^{[2
]}

机构：

[1] Karnatak Univ, Dept Chem, Dharwad 580003, Karnataka, India

[2] APL Res Ctr, Hyderabad 500072, India

来源：

ACS OMEGA | 2019年 / 4卷 / 03期

关键词：

1,3-DIPOLAR CYCLOADDITION REACTIONS; PYRAZOLE DERIVATIVES; ANTIMICROBIAL ACTIVITY; ANTIVIRAL ACTIVITY; ANTICANCER; INHIBITORS; ANTIBACTERIAL; SYDNONES; DESIGN; PYRIDAZINE;

D O I：

10.1021/acsomega.8b02013

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fused nitrogen heterocyclesnamely, pyrazolo[3,4-d]pyridazin-7(6H)-ones have been obtained by exploiting the 1,3-dipolar nature of N-arylsydnones, from hydrazones of 3-aryl-4-acetylsydnones via the Vilsmeier-Haack strategy. Facile intramolecular nucleophilic addition followed by CO2 elimination under reflux or upon microwave irradiation was presented. Plausible mechanisms for the formation of the title compounds are proffered. Structure confirmatory evidence came from single-crystal X-ray crystallography.

引用

页码：4955 / 4962

页数：8

共 50 条

[21] SYNTHESIS OF 3-ARYL-6H-ISOXAZOLO[3,4-D]PYRAZOLO[3,4-B]PYRIDINES AND 3-ARYL-6H-ISOXAZOLO[5,4-D]PYRAZOLO[3,4-B]PYRIDINES
SHUTSKE, GM
HUGER, FP
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (03) : 703 - 709
[22] STRUCTURE OF 1,5,6-TRIMETHYL-1H-PYRAZOLO[3,4-D]PYRIDAZINE-4,7(5H,6H)-DIONE
LEBAN, I
GOLIC, L
STANOVNIK, B
TISLER, M
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1988, 44 : 193 - 195
[23] VERSATILE SYNTHESIS OF 6-ALKYL-1H-PRYAZOLO[3,4-D]PYRIMIDIN-4[5H]-ONES AND 6-ARYL-1H-PYRAZOLO[3,4-D]PYRIMIDIN-4[5H]-ONES
REDDY, KH
REDDY, AP
VEERANAGAIAH, V
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1992, 31 (03): : 163 - 166
[24] SYNTHESIS OF 1-HYDROXY-2,4-DIPHENYLPYRROLO[2,3-D]PYRIDAZIN-7(6H)ONE
MIGLIARA, O
PETRUSO, S
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (01) : 203 - 203
[25] STUDIES ON PYRAZOLO[3,4-D]PYRIMIDINE DERIVATIVES .5. TRANSFORMATION OF PYRAZOLO[3,4-D]PYRIMIDINES-H-1 INTO PYRAZOLO[3,4-B]PYRIDINES-H-1
HIGASHINO, T
IWAI, Y
HAYASHI, E
CHEMICAL & PHARMACEUTICAL BULLETIN, 1977, 25 (04) : 535 - 542
[26] Synthesis 3,4-diamino-1H-pyrazolo[3,4-d]pyrimidines
Tumkyavichius, S
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1996, (06): : 831 - 836
[27] STUDIES ON 1H-ALKYLPYRAZOLO AND 2H-N-ALKYLPYRAZOLO[3,4-D]PYRIDAZIN-4(5H)ONES
GELIN, S
HARTMANN, D
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1978, 15 (05) : 813 - 816
[28] Synthesis of pyrazolo[3,4-d]-4,5-dihydropyrimidin-6-ones
Ryabukhin, Sergey V.
Granat, Dmitry S.
Plaskon, Andrey S.
Shivanyuk, Alexander
Lukin, Oleg
TETRAHEDRON LETTERS, 2014, 55 (10) : 1846 - 1847
[29] STUDIES ON PYRAZOLO[3,4-D]PYRIMIDINE DERIVATIVES .4. ON 1-METHYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE AND 1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE 5-OXIDE
HIGASHINO, T
IWAI, Y
HAYASHI, E
CHEMICAL & PHARMACEUTICAL BULLETIN, 1976, 24 (12) : 3120 - 3134
[30] SYNTHESIS AND ANTI-INFLAMMATORY PROPERTIES OF SOME PYRROLO(H-1,H-3)[3,4-D]PYRIMIDIN-2-ONES AND PYRROLO(H-1,H-6)[3,4-D]PYRIMIDIN-2-ONES
TARZIA, G
PANZONE, G
SCHIATTI, P
SELVA, D
FARMACO-EDIZIONE SCIENTIFICA, 1979, 34 (04): : 316 - 330

← 1 2 3 4 5 →