UNEXPECTED SELECTIVE REDUCTION OF 3- AND 6-HALOGENQUINOLINES AND 2‑BROMO-1-METHYLBENZIMIDAZOLE WITH RED PHOSPHORUS IN THE KOH/DMSO SYSTEM

V. A. Kuimov; Куимов В. А.; S. F. Malysheva; Малышева С. Ф.; N. A. Belogorlova; Белогорлова Н. А.; B. A. Trofimov; Трофимов Б. А.

doi:10.31857/S2686953522600416

UNEXPECTED SELECTIVE REDUCTION OF 3- AND 6-HALOGENQUINOLINES AND 2‑BROMO-1-METHYLBENZIMIDAZOLE WITH RED PHOSPHORUS IN THE KOH/DMSO SYSTEM

Authors: Kuimov V.A.¹, Malysheva S.F.¹, Belogorlova N.A.¹, Trofimov B.A.¹
Affiliations:
1. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
Issue: Vol 509, No 1 (2023)
Pages: 30-33
Section: CHEMISTRY
URL: https://ogarev-online.ru/2686-9535/article/view/135957
DOI: https://doi.org/10.31857/S2686953522600416
EDN: https://elibrary.ru/OVAIBL
ID: 135957

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Abstract

3-Bromo- and 6-chloroquinolines or 2-bromo-1-methylbenzimidazole react with red phosphorus in the KOH/DMSO (Н₂О) system upon heating (100–120°C, 3 h), forming selective reduction products in high yield (with preservation of the aromatic heterocycle), forming quinoline and 1-methylbenzimidazole, correspondingly.

Keywords

red phosphorus, superbases, 3-bromoquinoline, 6-chloroquinoline, 2‑bromo-1-methylbenzimidazole, reduction

About the authors

V. A. Kuimov

Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: boris_trofimov@irioch.irk.ru
Russian, 664033, Irkutsk

S. F. Malysheva

Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: boris_trofimov@irioch.irk.ru
Russian, 664033, Irkutsk

N. A. Belogorlova

Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: boris_trofimov@irioch.irk.ru
Russian, 664033, Irkutsk

B. A. Trofimov

Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Author for correspondence.
Email: boris_trofimov@irioch.irk.ru
Russian, 664033, Irkutsk

References

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