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POCl.sub.3./sub. mediated one-pot deoxygenative aromatization and electrophilic chlorination of dihydroxy-2-methyl-4-oxo-indeno[1,2-b]pyrroles
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SYSNO ASEP 0573800 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title POCl3 mediated one-pot deoxygenative aromatization and electrophilic chlorination of dihydroxy-2-methyl-4-oxo-indeno[1,2-b]pyrroles Author(s) Nasuhipur, A. (IR)
Ghasemi, Z. (IR)
Poupon, Morgane (FZU-D) ORCID
Dušek, Michal (FZU-D) RID, ORCID, SAINumber of authors 4 Source Title RSC Advances. - : Royal Society of Chemistry
Roč. 13, č. 26 (2023), s. 17812-17816Number of pages 5 s. Language eng - English Country GB - United Kingdom Keywords indenopyrroles ; vicinal hydroxyl group ; crystal structure ; X-ray diffraction Subject RIV BM - Solid Matter Physics ; Magnetism OECD category Condensed matter physics (including formerly solid state physics, supercond.) R&D Projects LM2018096 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support FZU-D - RVO:68378271 UT WOS 001007514000001 EID SCOPUS 85162778648 DOI 10.1039/d3ra02515b Annotation 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. Workplace Institute of Physics Contact Kristina Potocká, potocka@fzu.cz, Tel.: 220 318 579 Year of Publishing 2024 Electronic address https://hdl.handle.net/11104/0344159
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