Reaction of 6Н-5-(4-Fluorophenyl)-3-(2-pyridyl)-1,2,4-triazine with 4,5-Difluoro-1,2-dehydrobenzene

被引：0

作者：

Rammohan, A. ^{[1
]}

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

Sayfutdinova, Yu. M. ^{[1
]}

Shtaitz, Y. K. ^{[1
,2
]}

Potapova, S. S. ^{[1
,2
]}

Slepukhin, P. A. ^{[1
,2
]}

Gaviko, V. S. ^{[1
,3
]}

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

Zyryanov, G. V. ^{[1
,2
]}

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

机构：

[1] Ural Fed Univ, Ekaterinburg 620002, Russia

[2] Russian Acad Sci, Inst Organ Synth, Ural Branch, Ekaterinburg 620219, Russia

[3] Russian Acad Sci, Inst Phys Met, Ural Branch, Ekaterinburg 620108, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2024年 / 94卷 / 09期

关键词：

1,2,4-triazines; 4,5-difluoro-1,2-dehydrobenzene; pyrido[1,2-<italic>a</italic>]indoles; domino transformation; 1,6-dihydro-1,2,4-triazine-6-ols; 1<italic>H</italic>-1,2,4-triazoles; X-ray diffraction analysis; DIELS-ALDER REACTION; POTASSIUM-AMIDE; 1,2,4-TRIAZINES; DIENOPHILES; COMPLEXES; AMINATION; DEMAND; ROUTE;

D O I：

10.1134/S1070363224090056

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

AbstractThe reaction of C6-unsubstituted 5-aryl-3-(2-pyridyl)-1,2,4-triazine with generated in situ difluoroaryne intermediate (4,5-difluoro-1,2-dehydrobenzene), previously unused for this aim, was studied. New transformations of the 1,2,4-triazine nucleus were discovered, which lead, along with the domino transformation product (10-(1,2,3-triazole-3-yl)pyrido[1,2-a]indole) natural for this transformation, to the formation of unexpected products, namely 1,3,5-tris-substituted 1,6-dihydro-1,2,4-triazin-6-ol and 1H-1,2,4-triazole. The structure of the products was confirmed by physicochemical methods, including X-ray diffraction analysis.

引用

页码：2255 / 2263

页数：9

共 31 条

[1] A direct route to 6,6′-disubstituted-2,2′-bipyridines by double Diels-Alder/retro Diels-Alder reaction of 5,5′-bi-1,2,4-triazines.: Part 29.: 1,2,4-triazines in organic synthesis
Branowska, D
[J]. MOLECULES, 2005, 10 (01) : 274 - 278
[2] An efficient 1,2,4-triazine-based route to the louisianin alkaloids
Catozzi, Nicola
Wasnaire, Pierre
Taylor, Richard J. K.
[J]. TETRAHEDRON LETTERS, 2008, 49 (18) : 2865 - 2868
[3] Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach
Catozzi, Nicola
Edwards, Michael G.
Raw, Steven A.
Wasnaire, Pierre
Taylor, Richard J. K.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) : 8343 - 8354
[4] Lithiacarboranes and 1,2,4-triazine 4-oxides:: SNH reactions and ring transformations
Chupakhin, ON
Prokhorov, AM
Kozhevnikov, DN
Rusinova, VL
Glukhov, IA
Starikova, ZA
Ol'shevskaya, VA
Kalinin, VN
Antipin, MY
[J]. RUSSIAN CHEMICAL BULLETIN, 2004, 53 (06) : 1223 - 1231
[5] CrysAlisPro, 2017, Data Collection, Reduction and Correction Program
[6] [4+2] CYCLO-ADDITIONS WITH INVERSE ELECTRON DEMAND .17. OXEPIN AND 2,7-DIMETHYLOXEPIN AS DIENOPHILES IN DIELS-ALDER CYCLO-ADDITIONS WITH INVERSE ELECTRON DEMAND
DHAR, R
HUHNERMANN, W
KAMPCHEN, T
OVERHEU, W
SEITZ, G
[J]. CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (01): : 97 - 102
[7] El-Gahami M.A., 2013, ORIENT J CHEM, V29, P911, DOI 10.13005/ojc/290308
[8] Gckel U., 1980, Tetrahedron Lett, V21, P599, DOI [10.1016/S0040-4039(01)85567-2, DOI 10.1016/S0040-4039(01)85567-2]
[9] SYNTHESIS OF ISOQUINOLINES BY CYCLOADDITION OF ARYNES TO 1,2,4-TRIAZINES
GONSALVES, AMD
MELO, TMVDPE
GILCHRIST, TL
[J]. TETRAHEDRON, 1992, 48 (33) : 6821 - 6826
[10] A PASE-based approach towards 12-(1H-1,2,3-triazol-1-yl)indolo[2,1-a]isoquinolines via the reaction of 3-(isoquinolin-1-yl)-1,2,4-triazines with benzyne
Gundala, Sravya
Guda, Mallikarjuna Reddy
Khasanov, Albert F.
Kopchuk, Dmitry S.
Krinochkin, Alexey P.
Santra, Sougata
Zyryanov, Grigory V.
Venkatapuram, Padmavathi
Garcia, Jarem Raul
Charushin, Valery N.
[J]. MENDELEEV COMMUNICATIONS, 2019, 29 (04) : 369 - 371

← 1 2 3 4 →