Abstract
The tricyclic ring system of the antiviral drug nevirapine has been employed to test the workability of the hydrated imidazoline ring expansion (HIRE) reaction which was previously exemplified for [1.4]oxazepine and [1.4]thiazepine counterparts. The imidazoline nucleus was grafted onto the lactam moiety of nevirapine in two high-yielding steps. Subsequent N-alkylation and the HIRE reaction proceeded as envisioned and delivered rare ring-expanded diarene-fused 1,4,7-triazecines with a diversity of alkyl substituents at the lactam nitrogen atom. These findings extend the scope of the HIRE reaction to the medicinally prominent [1.4]diazepine chemical space.
Original language | English |
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Pages (from-to) | 20-22 |
Journal | Tetrahedron Letters |
Volume | 60 |
Issue number | 1 |
Early online date | 17 Nov 2018 |
DOIs | |
Publication status | Published - 2019 |
Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry