A facile synthesis of triazine integrated antipyrine derivatives through ecofriendly approach

被引：14

作者：

Rammohan, Aluru ^{[1
]}

Reddy, Guda Mallikarjuna ^{[1
]}

Krinochkin, Alexey P. ^{[1
,2
]}

Kopchuk, Dmitry S. ^{[1
,2
]}

Savchuk, Maria, I ^{[1
]}

Shtaitz, Yaroslav K. ^{[1
]}

Zyryanov, Grigory, V ^{[1
,2
]}

Rusinov, Vladimir L. ^{[1
,2
]}

Chupakhin, Oleg N. ^{[1
,2
]}

机构：

[1] Ural Fed Univ, Dept Organ & Biomol Chem, Ekaterinburg 620002, Russia

[2] Russian Acad Sci, Ural Branch, Inst Organ Synth, Ekaterinburg, Russia

来源：

SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 02期

基金：

俄罗斯科学基金会;

关键词：

Antipyrine; nucleophilic substitution; solvent free synthesis; triazines; SOLVENT-FREE SYNTHESIS; SCHIFF-BASES; 1,2,4-TRIAZINES; 4-AMINOANTIPYRINE;

D O I：

10.1080/00397911.2020.1823993

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The present study describes a facile and solvent free synthesis of 1,2,4-triazine antipyrine derivatives (2a-f) in prominent yields (70-85%) over nucleophilic substitution of 5-carbonitrile triazines. Further, we strained to convert them into pyridine analogues (3a-f) overaza-Diels-Alder reaction with norbornadiene as dienophile but it was an unsuccessful attempt. It is an assumption we made that the antipyrine substituent primes the triazine electronically unfavorable at 1,2-azaposition. All the synthesized compounds were confirmed by using(1)H NMR,F-19 NMR,C-13 NMR and Mass spectral studies. Furthermore, this stated synthetic approach is ecofriendly as there are no toxic intermediates and also, the antipyrine derivatives can be aiding as promising templates for the development of new pharmaceutical scaffolds.

引用

页码：256 / 262

页数：7

共 37 条

[1] SYNTHESIS AND ANTI-HBV ACTIVITY OF 4-AMINOANTIPYRINE DERIVATIVES [J].

Abdel-Rahman, A. A. -H. ;

Ahmed, A. H. A. ;

Ramiz, M. M. M. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (01) :72-78

[2] Synthesis of Some New Thiazoles and Pyrazolo[1,5-a]pyrimidines Containing an Antipyrine Moiety [J].

Abdelhamid, Abdou O. ;

Afifi, Mamdouh A. M. .

SYNTHETIC COMMUNICATIONS, 2010, 40 (10) :1539-1550

[3] A novel aluminum-sensitive fluorescent chemosensor based on 4-aminoantipyrine: An experimental and theoretical study [J].

Alyaninezhad, Zohreh ;

Bekhradnia, Ahmadreza ;

Feizi, Nourollah ;

Arshadi, Sattar ;

Zibandeh, Mahmood .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2019, 212 :32-41

[4] Synthesis and Anti-Bacterial Activities of Some Novel Schiff Bases Derived from Aminophenazone [J].

Asiri, Abdullah M. ;

Khan, Salman A. .

MOLECULES, 2010, 15 (10) :6850-6858

[5]

Attallah G. B., 2018, [No title captured], Patent No. [US20180305348A1, 20180305348]

[6]

Bodendorf K., 1959, ARCH PHARM, V292, DOI [10.1002/ardp.19592921011, DOI 10.1002/ARDP.19592921011]

[7]

Brune K., 1997, Acute Pain, V1, P33, DOI [DOI 10.1016/S1366-0071(97)80033-2, 10.1016/S1366-0071(97)80033-2]

[8]

Bunker K. D., 2020, [No title captured], Patent No. [US10513509B2, 10513509]

[9]

Charushin V. N., 2014, TOP HETEROCYCL CHEM, V37, P1, DOI DOI 10.1007/7081_2013_119

[10]

Chupakhin ON, 1997, MENDELEEV COMMUN, P66

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