Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion.
Imidazoline-fused [1,4]oxazepines (prepared in two simple steps from methyl 2-hydroxyaroates, ethylene diamine and bis-electrophilic aromatics) undergo a facile, good-yielding hydrolytic imidazoline ring expansion (HIRE) upon N-alkylation and treatment with aqueous K2CO3. The resulting arene-fused ten-membered lactams significantly add to the contemporary arsenal of small-molecule scaffolds where medium-sized ring systems are severely underrepresented.
Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii prospekt, Peterhof 198504, Russia. m.krasavin@spbu.ru.
Alexander
A
Sapegin
Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii prospekt, Peterhof 198504, Russia. m.krasavin@spbu.ru.
Angelina
A
Osipyan
Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii prospekt, Peterhof 198504, Russia. m.krasavin@spbu.ru.
Mikhail
http://orcid.org/0000-0002-0200-4772
M
Krasavin