Tandem Michael addition/elimination – novel reactivity of pyridinium ylides in reaction with electron-deficient alkenes

Tandem Michael addition/elimination – novel reactivity of pyridinium ylides in reaction with electron-deficient alkenes Full article

Journal

Organic Chemistry Frontiers
ISSN: 2052-4110 , E-ISSN: 2052-4129

Output data

Year: 2022, Volume: 9, Number: 18, Pages: 4998-5004 Pages count : 7 DOI: 10.1039/d2qo00911k

Authors

Izmest'ev Alexei N. ¹ , Motornov Vladimir A. ² , Vinogradov Dmitry B. ¹ , Ioffe Sema L. ¹ , Kravchenko Angelina N. ¹ , Gazieva Galina A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation
2	Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, 160 00 Prague 6, Czech Republic

Novel reactivity of pyridinium ylides in reaction with annulated 4-oxothiazolidin-5-ylidenes as electron-deficient alkenes involving a cascade Michael addition/elimination process is described. The method provides a broad variety of functionalized products available from dipolarophiles with different substituents within the heterocyclic system as well as pyridinium salts with different electron-withdrawing groups (EWG = CO2R, COPh, COMe, CN) in mild conditions with good to excellent yields.

Izmest'ev A.N. , Motornov V.A. , Vinogradov D.B. , Ioffe S.L. , Kravchenko A.N. , Gazieva G.A.
Tandem Michael addition/elimination – novel reactivity of pyridinium ylides in reaction with electron-deficient alkenes
Organic Chemistry Frontiers. 2022. V.9. N18. P.4998-5004. DOI: 10.1039/d2qo00911k WOS Scopus OpenAlex

≡ Web of science:	WOS:000839576200001
≡ Scopus:	2-s2.0-85136296536
≡ OpenAlex:	W4289981707