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Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo-trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates

Author:
Maslivetc, Vladimir A., Frolova, Liliya V., Rogelj, Snezna, Maslivetc, Anna A., Rubina, Marina, Rubin, Michael
Source:
Journal of organic chemistry 2018 v.83 no.22 pp. 13743-13753
ISSN:
1520-6904
Subject:
Lewis bases, amines, antineoplastic activity, carbamates, chemical reactions, chemical structure, organic chemistry, regioselectivity
Abstract:
A strain-release-driven, cation-templated nucleophilic 7- and 8-exo-trig-cyclization of tethered Boc-protected amines to cyclopropenes is described. The featured reaction proceeds in diastereo- and regioselective fashion and allows for preparation of the corresponding 2,5-diazabicyclo[5.1.0]octan-6-ones and 2,6-diazabicyclo[6.1.0]nonan-7-ones as sole products in high yields. Preliminary studies on anticancer activities of these novel cyclopropane-fused medium heterocycles were performed.
Agid:
6212482