Copper‐Mediated Oxidative [3+2]‐Annulation of Nitroalkenes and Ylides of 1,2‐Diazines: Assembly of Functionalized Pyrrolo[1,2‐b]pyridazines

Copper‐Mediated Oxidative [3+2]‐Annulation of Nitroalkenes and Ylides of 1,2‐Diazines: Assembly of Functionalized Pyrrolo[1,2‐b]pyridazines Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2021, Volume: 6, Number: 37, Pages: 9969-9974 Pages count : 6 DOI: 10.1002/slct.202103189

Authors

Motornov Vladimir A. ¹ , Tabolin Andrey A. ¹ , Nenajdenko Valentine G. ² , Ioffe Sema L. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, 119991 Russia
2	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow, 119991, Russia

Oxidative [3+2]-annulation reactions between nitroalkenes and pyridazinium ylides mediated by Cu(OAc)2⋅H2O were investigated. Functionalized pyrrolo[1,2-b]pyridazines and pyrrolo[1,2-a]phthalazines were accessed via this route. Starting from α-fluoronitroalkenes the reaction provides the first preparative synthesis of a broad scope of 5-fluoro-pyrrolo[1,2-b]pyridazines. The substrate scope in the case of α-unsubstituted nitroalkenes was investigated. Mechanistic features of the oxidative annulation reaction were studied to support the stepwise [3+2]-cycloaddition/oxidation/HNO2 elimination mechanism. Partially saturated primary [3+2]-adducts were isolated and characterized as key intermediates.

Motornov V.A. , Tabolin A.A. , Nenajdenko V.G. , Ioffe S.L.
Copper‐Mediated Oxidative [3+2]‐Annulation of Nitroalkenes and Ylides of 1,2‐Diazines: Assembly of Functionalized Pyrrolo[1,2‐b]pyridazines
ChemistrySelect. 2021. V.6. N37. P.9969-9974. DOI: 10.1002/slct.202103189 WOS Scopus OpenAlex

≡ Web of science:	WOS:000704246900031
≡ Scopus:	2-s2.0-85116470357
≡ OpenAlex:	W3203466431