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- Title
Cycloamidination of Aminoalkenes with Nitriles: Synthesis of Substituted 2-Imidazolines and Tetrahydropyrimidines.
- Authors
Huang, Shujian; Shao, Yinlin; Zhang, Lixin; Zhou, Xigeng
- Abstract
The first catalytic cycloamidination of aminoalkenes with nitriles has been achieved by using rare-earth complexes. This reaction is equivalent to the desired intramolecular hydroamination of alkenylamidines, and allows a new direct access to substituted 2-imidazolines and tetrahydropyrimidines in high yields under operationally simple reaction conditions. Moreover, the methodology is also efficient for synthesis of symmetric and unsymmetric bridged diimidazolines. Compared with the traditional stepwise-mediated synthetic approaches, the present method avoids the use of additives and harsh reaction conditions, and thus leads to a completely different product distribution. Mechanistic data suggest that the reaction involves the initial NH activation by lanthanide complex followed by nitrile insertion into a Ln-N bond to form an amidinate lanthanide intermediate which undergoes the cyclization.
- Subjects
ALKENES; NITRILES; IMIDAZOLINES; ANTIPARASITIC agents; RARE earth metal compounds; HYDROAMINATION
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 48, p14660
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201508442