Antiviral drug nevirapine as a template for hydrated imidazoline ring expansion (HIRE)

Rapid access to the diarene-fused 1,4,7-triazecine ring system

Research outputpeer-review

1 Citation (Scopus)

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 languageEnglish
Pages (from-to)20-22
JournalTetrahedron Letters
Volume60
Issue number1
DOIs
Publication statusPublished - 2019

Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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title = "Antiviral drug nevirapine as a template for hydrated imidazoline ring expansion (HIRE): Rapid access to the diarene-fused 1,4,7-triazecine ring system",
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.",
keywords = "1,4,7-triazecines, Hydrated imidazoline ring expansion, Medium-sized rings, Nevirapine, [1.4]diazepines",
author = "Sergey Grintsevich and Alexander Sapegin and Elena Reutskaya and Mikhail Krasavin",
year = "2019",
doi = "10.1016/j.tetlet.2018.11.044",
language = "English",
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pages = "20--22",
journal = "Tetrahedron Letters",
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number = "1",

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T1 - Antiviral drug nevirapine as a template for hydrated imidazoline ring expansion (HIRE)

T2 - Rapid access to the diarene-fused 1,4,7-triazecine ring system

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

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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

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