Diaziridine ring expansion in 6-aryl-1,5-diazabicyclo[3.1.0]hexanes upon reactions with activated olefins in ionic liquids

Diaziridine ring expansion in 6-aryl-1,5-diazabicyclo[3.1.0]hexanes upon reactions with activated olefins in ionic liquids Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2010, Volume: 59, Number: 8, Pages: 1621-1630 Pages count : 10 DOI: 10.1007/s11172-010-0286-x

Authors

Syroeshkina Yu.S. ¹ , Fershtat L.L. ¹ , Kachala V.V. ¹ , Kuznetsov V.V. ¹ , Makhova N.N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

Reactions of 1,3-diphenylpropen-2-one and α-nitrostyrenes with azomethine imines, generated from 6-aryl-1,5-diazabicyclo[3.1.0]hexanes on catalysis with Et2O•BF3 in ionic liquids, were found to proceed with high regio- and stereoselectivity to afford the products of the diaziridine ring expansion, viz., [3-aryl-2-phenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol- 1-yl](phenyl)methanones, 1,3-diaryl-2-nitrotetrahydro-1H,5H-pyrazolo[1,2-a]pyrazoles and 5-aryl-6-(3-nitrophenyl)-2,3-dihydro-1H-pyrazolo[1,2-a]pyrazolium tetrafluoroborates (hexafluorophosphates). The reactions discovered are new, more simple methods for the syn- thesis of bicyclic structures.

Syroeshkina Y.S. , Fershtat L.L. , Kachala V.V. , Kuznetsov V.V. , Makhova N.N.
Diaziridine ring expansion in 6-aryl-1,5-diazabicyclo[3.1.0]hexanes upon reactions with activated olefins in ionic liquids
Russian Chemical Bulletin. 2010. V.59. N8. P.1621-1630. DOI: 10.1007/s11172-010-0286-x WOS Scopus OpenAlex

Web of science:	WOS:000285876500021
Scopus:	2-s2.0-79951742619
OpenAlex:	W1979825278

DB	Citing
OpenAlex	12
Scopus	12
Web of science	15