Generation and metathesis of azomethine imines in reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with het(aryl)methylidenemalononitriles

Generation and metathesis of azomethine imines in reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with het(aryl)methylidenemalononitriles Full article

Journal

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

Output data

Year: 2013, Volume: 62, Number: 4, Pages: 1066-1075 Pages count : 10 DOI: 10.1007/s11172-013-0143-9

Authors

Pleshchev M.I. ¹ , Petukhova V.Yu. ¹ , Kuznetsov V.V. ¹ , Khakimov D.V. ¹ , Pivina T.S. ¹ , Nelyubina Yu.V. ² , Makhova N.N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russian Federation

A new metathesis reaction of azomethine imines is found. Catalytic or thermal diaziridine ring opening of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes leads to azomethine imines reacting further with het(aryl)methylidenemalononitriles to give in situ new azomethine imines inaccessible by common synthetic methods. New azomethine imines are detected as pyrazolines formed via a 1,4-H shift and trapped by the [3+2] cycloaddition with various dipolarophiles to yield 1,5-diazabicyclo[3.3.0]octane derivatives bearing pharmacophoric heterocycles, e.g. furan, nitrofuran, thiophene, and indole. The best results are achieved in the Et2O·BF3-catalyzed reactions in ionic liquids.

Pleshchev M.I. , Petukhova V.Y. , Kuznetsov V.V. , Khakimov D.V. , Pivina T.S. , Nelyubina Y.V. , Makhova N.N.
Generation and metathesis of azomethine imines in reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with het(aryl)methylidenemalononitriles
Russian Chemical Bulletin. 2013. V.62. N4. P.1066-1075. DOI: 10.1007/s11172-013-0143-9 WOS Scopus OpenAlex

Web of science:	WOS:000331392200026
Scopus:	2-s2.0-84897724446
OpenAlex:	W2066270311

DB	Citing
OpenAlex	13
Scopus	11
Web of science	11