Direct transition-metal-free synthesis of 2-heteroaryl-4-quinolones <i>via</i> ANRORC type rearrangement of 3-(2-(2-nitrophenyl)-2-oxoethyl)quinoxalin-2(1 <i>H</i> )-ones
A novel, metal-free, reductive intramolecular ANRORC-type rearrangement of nitrobenzenes and unmodified imines has been developed, providing simple and direct access to a wide range of 2-(benzimidazol-2-yl)quinolin-4(1<i>H</i>)-ones <i>via</i> a transformation sequence involving N(sp<sup>3</sup>)-H functionalization/N(sp<sup>3</sup>)-C(sp<sup>2</sup>) bond formation <i>via</i> nucleophilic addition/ring opening with N(sp<sup>3</sup>)-C(sp<sup>3</sup>) bond cleavage/ring closure with C(sp<sup>2</sup>)-C(sp<sup>2</sup>) bond formation from readily accessible 3-(2-(2-nitrophenyl)-2-oxoethyl)quinoxalin-2(1<i>H</i>)-ones, using sodium dithionite as a reducing agent. The utility of this methodology is further demonstrated in the synthesis of 2-(imidazo[4,5-<i>b</i>]pyridin-2-yl)quinolin-4(1<i>H</i>)-one, 2-(purin-8-yl)quinolin-4(1<i>H</i>)-one and 2-(imidazole-2-yl)quinolin-4(1<i>H</i>)-one hybrids as well as the 2,2'-([5,5'-bibenzimidazole]-2,2'-diyl)bis(quinolin-4(1<i>H</i>)-one) scaffold.
Authors
- Oleg Gerol'dovich Sinyashin (ORCID: https://orcid.org/0000-0002-2241-9764)
- Victor V. Syakaev (ORCID: https://orcid.org/0000-0002-3516-1969)
- Venera R. Galimullina
- А.Т. Губайдуллин (ORCID: https://orcid.org/0000-0002-8114-7025)
- И. Х. Ризванов (ORCID: https://orcid.org/0000-0001-7417-7106)
- Olga B. Babaeva (ORCID: https://orcid.org/0000-0001-8567-9873)
- В. А. Мамедов (ORCID: https://orcid.org/0000-0001-8584-8999)
- Dariya V. Nikolaeva
Institutions
- A.E. Arbuzov Institute of Organic and Physical Chemistry (RU)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob01303h
- Citations
- 1
- Primary Topic
- Synthesis and Biological Evaluation
- Type
- article
- Field-Weighted Citation Impact
- 0.94