POCl.sub.3./sub. mediated one-pot deoxygenative aromatization and electrophilic chlorination of dihydroxy-2-methyl-4-oxo-indeno[1,2-b]pyrroles

0573800 - FZÚ 2024 RIV GB eng J - Journal Article
Nasuhipur, A. - Ghasemi, Z. - Poupon, Morgane - Dušek, Michal
POCl₃ mediated one-pot deoxygenative aromatization and electrophilic chlorination of dihydroxy-2-methyl-4-oxo-indeno[1,2-b]pyrroles.
RSC Advances. Roč. 13, č. 26 (2023), s. 17812-17816. E-ISSN 2046-2069
R&D Projects: GA MŠMT(CZ) LM2018096
Institutional support: RVO:68378271
Keywords : indenopyrroles * vicinal hydroxyl group * crystal structure * X-ray diffraction
OECD category: Condensed matter physics (including formerly solid state physics, supercond.)
Impact factor: 3.9, year: 2022
Method of publishing: Open access

A class of indenopyrroles is presented by the treatment of known dihydroxy-2-methyl-4-oxoindeno[1,2-b] pyrroles with phosphorus oxychloride (POCl3). The elimination of vicinal hydroxyl groups at the 3a and 8b positions, formation of a p bond, and electrophilic chlorination of the methyl group attached to C2 resulted in the fused aromatic pyrrole structures. Benzylic substitution of various nucleophiles such as H2O, EtOH, and NaN3 with a chlorine atom gave diverse 4-oxoindeno[1,2-b]pyrrole derivatives in 58 to 93% yields. The reaction was investigated in different aprotic solvents, and the highest reaction yield was obtained in DMF. The structures of the products were confirmed by spectroscopic methods, elemental analysis, and X-ray crystallography.
Permanent Link: https://hdl.handle.net/11104/0344159