Synthesis of 1,2,3,4‐Tetrazine 1,3‐Dioxides Annulated with 1,3 a,4,6 a‐Tetraazapentalene Systems

Synthesis of 1,2,3,4‐Tetrazine 1,3‐Dioxides Annulated with 1,3 a,4,6 a‐Tetraazapentalene Systems Full article

Journal

Asian Journal of Organic Chemistry
ISSN: 2193-5815 , E-ISSN: 2193-5807

Output data

Year: 2018, Volume: 7, Number: 12, Pages: 2534-2543 Pages count : 10 DOI: 10.1002/ajoc.201800545

Authors

Konnov Alexey A. ¹ , Klenov Michael S. ¹ , Churakov Aleksandr M. ¹ , Strelenko Yurii A. ¹ , Dmitrienko Artem O. ² , Puntus Lada N. ³ , Lyssenko Konstantin A. ⁴ , Tartakovsky Vladimir A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., 119991 Moscow, Russian Federation
3	V.A. Kotel'nikov Institute of Radioengineering and Electronics, Russian Academy of Sciences, 11-7 Mokhovaya St., 125009 Moscow, Russian Federation
4	Department of Chemistry, Lomonosov Moscow State University, 119992 Moscow, Russian Federation

A synthetic approach to 5,11-dehydro-5H,11H-[1,2,3,4]tetrazino[5′,6′:4,5][1,2,3]triazolo[2,1-a][1,2,3]benzotriazole 1,3-dioxide (5) and 5,11-dehydro-5H,11H-[1,2,3,4]tetrazino-[5′,6′:4,5][1,2,3]triazolo[2,1-a][1,2,3]benzotriazole 2,4-dioxide (6) was developed. These ring systems are the first in which a 1,2,3,4-tetrazine 1,3-dioxide ring is directly fused with 1,3a,4,6a-tetraazapentalene moiety. The synthesis started from (tert-butyl-NNO-azoxy)acetonitrile (7) and involved the closure of the 1,2,3,4-tetrazine 1,3-dioxide ring first and then formation of the tetraazapentalene ring. The derivatives of ring systems 5 and 6 nitrated at the benzene ring were also obtained. The structures of the compounds synthesized have been confirmed by NMR spectroscopy and X-ray diffraction studies.

Konnov A.A. , Klenov M.S. , Churakov A.M. , Strelenko Y.A. , Dmitrienko A.O. , Puntus L.N. , Lyssenko K.A. , Tartakovsky V.A.
Synthesis of 1,2,3,4‐Tetrazine 1,3‐Dioxides Annulated with 1,3 a,4,6 a‐Tetraazapentalene Systems
Asian Journal of Organic Chemistry. 2018. V.7. N12. P.2534-2543. DOI: 10.1002/ajoc.201800545 WOS Scopus OpenAlex

≡ Web of science:	WOS:000453384700027
≡ Scopus:	2-s2.0-85056595211
≡ OpenAlex:	W2899468921