Interaction of 3,6-Bis(2-pyridyl)-1,2,4,5-tetrazine and 3,4,5,6-Tetrabromo-1,2-dehydrobenzene

被引：0
作者：
Vatolina, S. E. [1 ]
Krinochkin, A. P. [1 ,2 ]
Rybakova, A. V. [3 ]
Khalymbadzha, I. A. [1 ]
Gaviko, V. S. [1 ,4 ]
Kopchuk, D. S. [1 ,2 ]
Zyryanov, G. V. [1 ,2 ]
机构：
[1] Ural Fed Univ, Ekaterinburg 620002, Russia
[2] Russian Acad Sci, Inst Organ Synth, Ural Branch, Ekaterinburg 620219, Russia
[3] South Ural State Univ, Chelyabinsk 454080, Russia
[4] Russian Acad Sci, Inst Phys Met, Ural Branch, Ekaterinburg 620108, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 61卷 / 06期
关键词：
1,2,4,5-tetrazines; 3,4,5,6-tetrabromo-1,2-dehydrobenzene; aza-Diels-Alder reaction; 3,6-disubstituted pyridazines; X-ray structural analysis; DIELS-ALDER REACTIONS; 1,2,4-TRIAZINES; DIENOPHILES;
D O I：
10.1134/S1070428025602043
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The interaction of 3,6-bis(2-pyridyl)-substituted 1,2,4,5-tetrazine with 3,4,5,6-tetrabromo-1,2-dehydrobenzene obtained in situ from the corresponding anthranilic acid was studied for the first time. In this case, instead of the expected product, 5,6,7,8-tetrabromo-1,4-di(2-pyridyl)phthalazine, two alternative transformation products were found, namely 1,2,3,4-tetrabromo-6-methylnaphthalene and 3,6-di(2-pyridyl)pyridazine. The structure of the products was confirmed by physicochemical methods, including X-ray diffraction data. A possible mechanism for this interaction was proposed.
引用
收藏
页码：1127 / 1133
页数：7
相关论文
共 33 条
[1]   INDOLE AS A DIENOPHILE IN INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS - REACTIONS WITH 1,2,4-TRIAZINES AND 1,2-DIAZINES [J].
BENSON, SC ;
GROSS, JL ;
SNYDER, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3257-3269
[2]   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 [J].
Branowska, D .
MOLECULES, 2005, 10 (01) :274-278
[3]  
CrysAlisPro, 2017, Data Collection, Reduction and Correction Program
[4]  
Ghumaan S., 2005, CCDC 256270: Experimental Crystal Structure Determination, DOI [10.5517/cc8lns8, DOI 10.5517/CC8LNS8]
[5]   PROBLEM OF VALENCE ISOMERIZATION - 4H-AZEPINES AND 3-AZANORCARADIENES [J].
GOCKEL, U ;
HARTMANNSGRUBER, U ;
STEIGEL, A ;
SAUER, J .
TETRAHEDRON LETTERS, 1980, 21 (07) :599-602
[6]   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 [J].
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. .
MENDELEEV COMMUNICATIONS, 2019, 29 (04) :369-371
[7]   ARYNE CHEMISTRY .28. SOME FURTHER CYCLOADDITION REACTIONS OF TETRAHALOGENOBENZYNES GENERATED FROM TETRAHALOGENOANTHRANILIC ACIDS [J].
HEANEY, H ;
MASON, KG ;
SKETCHLEY, JM .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (03) :567-+
[8]  
Holzer W., 2004, Science of Synthesis: Hetarenes and Related Ring Systems, V16, P315, DOI [10.1055/sos-SD-016-0038, DOI 10.1055/SOS-SD-016-0038]
[9]   One-step synthesis of 1,4-bis(het)arylisoquinolines by the reaction of 1,2,4-triazines with arynes [J].
Kopchuk, Dmitry S. ;
Nikonov, Igor L. ;
Khasanov, Albert F. ;
Gundala, Sravya ;
Krinochkin, Alexey P. ;
Slepukhin, Pavel A. ;
Zyryanov, Grigory V. ;
Venkatapuram, Padmavathi ;
Chupakhin, Oleg N. ;
Charushin, Valery N. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (10) :978-984
[10]   Studies on the interactions of 5-R-3-(2-pyridyl)-1,2,4-triazines with arynes: inverse demand aza-Diels-Alder reaction versus aryne-mediated domino process [J].
Kopchuk, Dmitry S. ;
Nikonov, Igor L. ;
Khasanov, Albert F. ;
Giri, Kousik ;
Santra, Sougata ;
Kovalev, Igor S. ;
Nosova, Emiliya V. ;
Gundala, Sravya ;
Venkatapuram, Padmavathi ;
Zyryanov, Grigory V. ;
Majee, Adinath ;
Chupakhin, Oleg N. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (28) :5119-5135
1234