Premium
A Ring Expansion Route to Benzofused N‐Heterocycles Through Aryne Insertion into 1,3‐Diaza‐heterocycles
Author(s) -
Yang Yun,
Xu Yue,
Jones Christopher R.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900570
Subject(s) - aryne , chemistry , ring (chemistry) , stereochemistry , transformation (genetics) , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , gene
Arynes have been found to undergo formal σ‐bond insertion into a C(sp3)–N bond for the first time. This transformation is utilized in the ring expansion of 1,3‐diaza‐heterocycles to afford benzofused medium‐ring N‐heterocycles in a single step. This represents a novel route to biologically relevant 2,3,4,5‐tetrahydro‐1 H ‐benzo[ e ][1,4]diazepines, prepared directly from easily accessible imidazolidines. An example of the ring expansion of a 1,3‐diazetidine is also reported, which affords the corresponding 1,2,3,4‐tetrahydroquinazoline.