Design of hybrid heterocyclic systems with a furoxanylpyridine core via tandem hetero-Diels–Alder/retro-Diels–Alder reactions of (1,2,4-triazin-3-yl)furoxans

Design of hybrid heterocyclic systems with a furoxanylpyridine core via tandem hetero-Diels–Alder/retro-Diels–Alder reactions of (1,2,4-triazin-3-yl)furoxans Full article

Journal

RSC Advances
ISSN: 2046-2069

Output data

Year: 2016, Volume: 6, Number: 37, Pages: 31526-31539 Pages count : 14 DOI: 10.1039/c6ra05110c

Authors

Fershtat Leonid L. ¹ , Larin Alexander A. ¹ , Epishina Margarita A. ¹ , Ovchinnikov Igor V. ¹ , Kulikov Alexander S. ¹ , Ananyev Ivan V. ² , Makhova Nina N. 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 Str., 119991 Moscow, Russian Federation

Two convenient, facile, regioselective and highly effective one-pot protocols for the synthesis of previously unknown hybrid heterocyclic systems with the furoxanylpyridine core based on the tandem inverse-electron-demand hetero-Diels–Alder/retro-Diels–Alder reactions of the tailor-made (1,2,4-triazin-3-yl)furoxans with 1-(pyrrolidino)cyclohexene and norbornadiene have been developed. The methods comprise [4 + 2] cycloaddition of enamine or norbornadiene to the 1,2,4-triazine ring of (1,2,4-triazin-3-yl)furoxans followed by one-pot transformation of the formed intermediates and this affords an extensive series of polyheterocyclic ensembles combining furoxan and pyridine (tetrahydroisoquinoline, indenopyridine, terpyridine) rings in one molecule through a C–C bond in good to excellent yields.

Fershtat L.L. , Larin A.A. , Epishina M.A. , Ovchinnikov I.V. , Kulikov A.S. , Ananyev I.V. , Makhova N.N.
Design of hybrid heterocyclic systems with a furoxanylpyridine core via tandem hetero-Diels–Alder/retro-Diels–Alder reactions of (1,2,4-triazin-3-yl)furoxans
RSC Advances. 2016. V.6. N37. P.31526-31539. DOI: 10.1039/c6ra05110c WOS Scopus OpenAlex

Web of science:	WOS:000373118200095
Scopus:	2-s2.0-84962129216
OpenAlex:	W2303039462

DB	Citing
OpenAlex	52
Scopus	50
Web of science	50