Lvov, Andrey G.’s team published research in Organic & Biomolecular Chemistry in 2019 | CAS: 16441-28-4

Organic & Biomolecular Chemistry published new progress about Benzannulation. 16441-28-4 belongs to class thiazole, name is 2-(2-Phenylthiazol-4-yl)acetic acid, and the molecular formula is C11H9NO2S, Application In Synthesis of 16441-28-4.

Lvov, Andrey G. published the artcilePhotorearrangement of dihetarylethenes as a tool for the benzannulation of heterocycles, Application In Synthesis of 16441-28-4, the main research area is bromo heteroarylethanone heteroaryl acetic acid cyclocondensation reaction; diheteroaryl furanone preparation tandem benzannulation photorearrangement; heteroaryl fused benzofuranone preparation crystal structure.

A general strategy for the preparative benzannulation of aromatic heterocycles via photocyclization of 1,2-dihetarylethenes was proposed for the first time. The strategy included two steps namely, modular assembly of dihetarylethenes from widely available 3-hetarylacetic acids and 2-bromo-1-hetarylethanones and subsequent preparative photorearrangement (using a UV lamp at 365 nm as the light source). This approach was efficient for the annulation of a wide range of heterocycles and provided C-, N-, O- or S-substituents in the benzoheterocycles obtained. The photochem. step was a metal-, acid- and oxidant-free reaction, which required non-inert conditions and easily monitored by NMR spectroscopy. Applicability of the proposed strategy was tested in the synthesis of a wide range of substituted carbazoles and benzo[b]thiophenes as well as on a gram-scale benzannulation of 3-indoleacetic acid. This study disclosed how to overcome two notable obstacles to the successful photorearrangement of dihetarylethenes: undesired reactions associated with photogenerated singlet oxygen and the instability of desired products. The first problem was successfully solved by the addition of DABCO, while development of an in-situ alkylation protocol to trap unstable photoproducts allowed us to overcome the second issue.

Organic & Biomolecular Chemistry published new progress about Benzannulation. 16441-28-4 belongs to class thiazole, name is 2-(2-Phenylthiazol-4-yl)acetic acid, and the molecular formula is C11H9NO2S, Application In Synthesis of 16441-28-4.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica