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.
| Language | English |
|---|---|
| Pages | 20-22 |
| Journal | Tetrahedron Letters |
| Volume | 60 |
| Issue number | 1 |
| DOIs | |
| State | Published - 2019 |
Keywords
- 1,4,7-triazecines
- Hydrated imidazoline ring expansion
- Medium-sized rings
- Nevirapine
- [1.4]diazepines
Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
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Antiviral drug nevirapine as a template for hydrated imidazoline ring expansion (HIRE) : Rapid access to the diarene-fused 1,4,7-triazecine ring system. / Grintsevich, Sergey; Sapegin, Alexander; Reutskaya, Elena; Krasavin, Mikhail.
In: Tetrahedron Letters, Vol. 60, No. 1, 2019, p. 20-22.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - Antiviral drug nevirapine as a template for hydrated imidazoline ring expansion (HIRE)
T2 - Tetrahedron Letters
AU - Grintsevich, Sergey
AU - Sapegin, Alexander
AU - Reutskaya, Elena
AU - Krasavin, Mikhail
PY - 2019
Y1 - 2019
N2 - 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.
AB - 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.
KW - 1,4,7-triazecines
KW - Hydrated imidazoline ring expansion
KW - Medium-sized rings
KW - Nevirapine
KW - [1.4]diazepines
UR - http://www.scopus.com/inward/record.url?scp=85056906714&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2018.11.044
DO - 10.1016/j.tetlet.2018.11.044
M3 - Article
VL - 60
SP - 20
EP - 22
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 1
ER -