An efficient and facile synthesis of new tetracyclic fused pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones

被引：4

作者：

Gomaa, Mohsen A. -M. ^{[1
]}

Ali, Huda A. ^{[1
]}

机构：

[1] Menia Univ, Dept Chem, Fac Sci, El Minia 61519, Egypt

来源：

MOLECULAR DIVERSITY | 2018年 / 22卷 / 04期

关键词：

Pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolone; Amidrazone; (1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile; Dearomatization; NITROGEN SYSTEMS BEARING; POTENTIAL ANTI-HIV; ENANTIOSELECTIVE CONSTRUCTION; 1,3-DIPOLAR CYCLOADDITIONS; 1,2,4-TRIAZINE MOIETY; ANTICANCER DRUGS; AMIDRAZONES; FLUORINE;

D O I：

10.1007/s11030-018-9849-9

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：

Reaction of amidrazones 1a-1i with (1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile (2) in ethyl acetate solution in one-step reaction led to the formation of unprecedented pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones 3a-3g along with pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-12b-oles 3h-3m in moderate to excellent yields. These novel heterocycles were formed via a Michael addition reaction followed by intramolecular cyclization via a dearomatization process.

引用

页码：969 / 977

页数：9

共 42 条

[1] An efficient and facile synthesis of new tetracyclic fused pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones
Mohsen A.-M. Gomaa
Huda A. Ali
Molecular Diversity, 2018, 22 : 969 - 977
[2] Synthesis, biological activity and molecular modeling study of novel 1,2,4-triazolo[4,3-b][1,2,4,5]tetrazines and 1,2,4-triazolo[4,3-b][1,2,4]triazines
El-Reedy, Ahmed A. M.
Soliman, N. K.
SCIENTIFIC REPORTS, 2020, 10 (01)
[3] Efficient Routes to Pyrazolo[3,4-e][1,2,4]triazines and a New Ring System: [1,2,4]Triazino[5,6-d][1,2,3]triazines
Al-Matar, Hamad Mohamed
Khalil, Khaled Dessouky
Al-Dorri, Doa'a Mohamed
Elnagdi, Mohamed Helmy
MOLECULES, 2010, 15 (05): : 3302 - 3310
[4] Synthesis and Pharmacological Studies of Unprecedented Fused Pyridazino[3′,4′:5,6][1,2,4]triazino[3,4-b][1,3,4]thiadiazine Derivatives
Ali, Rania S.
Saad, Hosam A.
MOLECULES, 2018, 23 (05):
[5] Synthesis of 2-(1,2,4-oxadiazol-5-yl)-2,3-dihydro-4H-chromen-4-ones
Kysil, Andrii, I
Biitseva, Angelina, V
Bugera, Oleksandra, I
Yegorova, Tetyana, V
Voitenko, Zoia V.
FRENCH-UKRAINIAN JOURNAL OF CHEMISTRY, 2020, 8 (02): : 176 - 182
[6] Rapid and facile synthesis of spiro[indole-3,3′-[1,2,4]triazol]-2(1H)-ones
Mohamed, Ashraf M.
Alsharari, Musaed A.
Aly, Ashraf A.
JOURNAL OF CHEMICAL RESEARCH, 2010, (04) : 200 - 202
[7] Synthesis of trifluoromethyl-promoted functional pyrazolo [1,5-a]pyrimidine and pyrazolo [5,1-d] [1,2,3,5]tetrazine-4(3H)-ones
Wu, YC
Chen, YJ
Li, HJ
Zou, XM
Hu, FZ
Yang, HZ
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (03) : 409 - 416
[8] A Novel Method for Synthesis of 7-Chloro-1H-Imidazo[5,1-c][1,2,4]Triazol-3-Amine from 4,5-Dichloroimidazole
A. S. Bunev
S. V. Naumov
V. E. Statsyuk
P. P. Purygin
Chemistry of Heterocyclic Compounds, 2012, 48 : 1415 - 1416
[9] A Novel Method for Synthesis of 7-Chloro-1H-Imidazo[5,1-c][1,2,4]Triazol-3-Amine from 4,5-Dichloroimidazole
Bunev, A. S.
Naumov, S. V.
Statsyuk, V. E.
Purygin, P. P.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (09) : 1415 - 1416
[10] Synthesis of Some 1-(Flavon-7-yl)-4,5-dihydro-1,2,4-triazin-6(1H)-ones and Related Congeners
Abu-Aisheh, Marwa N.
Mustafa, Mohammad S.
Mubarak, Mohammad S.
El-Abadelah, Mustafa M.
Voelter, Wolfgang
LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (07) : 465 - 473

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