Journal
RUSSIAN CHEMICAL BULLETIN
Volume 59, Issue 7, Pages 1451-1458Publisher
SPRINGER
DOI: 10.1007/s11172-010-0261-6
Keywords
alkynylchlorocyclopropanes; 1,2-diaminoethane; 1,3-diaminopropane; hexahydropyrrolo[1,2-a]imidazoles; octahydropyrrolo[1,2-a]pyrimidines; hexahydropyrimidines; elimination; nucleophilic addition; cyclopropane ring opening; cascade cyclization
Categories
Funding
- Council on Grants at the President of the Russian Federation [NSh 8242.2010.3]
- Russian Foundation for Basic Research [6-03-33045-a]
- Russian Academy of Sciences [OKh-01]
Ask authors/readers for more resources
A reaction of 1-alkynyl-1-chlorocyclopropanes with excess of lithium derivative of 1,2-diaminoethane leads to 5-methylidenehexahydropyrrolo[1,2-a]imidazoles in 35-72% yields, whereas analogous reaction with lithium derivative of 1,3-diaminopropane gives 6-methylideneoctahydropyrrolo[1,2-a]pyrimidine in up to 50% yield. A mechanism of these unusual multi-step processes includes dehydrochlorination of 1-alkynyl-1-chlorocyclopropanes to form conjugated alkynylcyclopropenes capable of addition of monoalkylamide ions at the double bond, leading to the corresponding secondary cyclopropylamines; the latter under the reaction conditions isomerize to the linear imines, which further undergo a cascade cyclization with sequential involvement of the C=N and C=C bonds.
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