An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes

An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2021, Volume: 26, Number: 12, Article number : 3515, Pages count : DOI: 10.3390/molecules26123515

Authors

Aldoshin Alexander S. ¹ , Tabolin Andrey A. ² , Ioffe Sema L. ² , Nenajdenko Valentine G. ¹

Affiliations

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

The catalyst-free conjugate addition of pyrroles to β-Fluoro-β-nitrostyrenes was investigated. The reaction was found to proceed under solvent-free conditions to form 2-(2-Fluoro-2-nitro-1-arylethyl)-1H-pyrroles. The effectiveness of this approach was demonstrated through the preparation of a series of the target products in a quantitative yield. The kinetics of a conjugate addition of pyrrole was studied in detail to reveal the substituent effect and activation parameters of the reaction. The subsequent base-induced elimination of nitrous acid afforded a series of novel 2-(2-Fluoro-1-arylvinyl)-1H-pyrroles prepared in up to an 85% isolated yield. The two-step sequence herein proposed is an indispensable alternative to a direct reaction with elusive and unstable 1-Fluoroacetylenes.

Aldoshin A.S. , Tabolin A.A. , Ioffe S.L. , Nenajdenko V.G.
An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes
Molecules. 2021. V.26. N12. 3515 . DOI: 10.3390/molecules26123515 WOS Scopus OpenAlex

≡ Web of science:	WOS:000666278900001
≡ Scopus:	2-s2.0-85108346949
≡ OpenAlex:	W3171856539