|Conţinutul numărului revistei|
| SM ISO690:2012|
CURLAT, Serghei; BARBĂ, Alic; BOLDESCU, Veaceslav; PANEKOK, K.; MACAEV, Fliur. Synthesis of Aminoalkylated Aziridines from (+)-3-Carene. In: Chemistry of Natural Compounds. 2019, nr. 2(55), pp. 269-274. ISSN 0009-3130.
|Chemistry of Natural Compounds|
|Numărul 2(55) / 2019 / ISSN 0009-3130|
Aminoalkylated carane-type aziridines were synthesized via epoxidation of (+)-3-carene by H 2 O 2 solution (7%) in EtOAc catalyzed by α-Al 2 O 3 nanoparticles, opening of the epoxide by NaN 3 , and cyclization of the azidoalcohol by Ph 3 P followed by condensation of the resulting aziridines with formalin and secondary amines. The cytotoxicity of the aminoalkylated aziridines with heteroorganic substituents increased on going from a five-membered pyrrolidine ring substituent to a six-membered piperidine ring and decreased sharply upon replacing a piperidine by a morpholine ring or increased on going to a piperazine ring. The structures of products were established using IR and NMR spectroscopy and an X-ray crystal structure analysis. .
( )-3-carene, aminoalkylation, aziridines, cytotoxicity