Journal
RUSSIAN CHEMICAL BULLETIN
Volume 62, Issue 4, Pages 1066-1075Publisher
SPRINGER
DOI: 10.1007/s11172-013-0143-9
Keywords
diaziridines; 6-aryl-1,5-diazabicyclo[3.1.0]hexanes; het(aryl)methylidenemalononitriles; azomethine imines; [3+2] cycloaddition; metathesis; cycloreversion; 1,5-diazabicyclo[3.3.0]octanes; pyrazolines; ionic liquids; boron trifluoride diethyl etherate; catalysis
Categories
Funding
- Russian Foundation for Basic Research [13-03-00153a]
- Presidium of Russian Academy of Sciences [8]
Ask authors/readers for more resources
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 center dot BF3-catalyzed reactions in ionic liquids.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available