POCl3 mediated one-pot deoxygenative aromatization and electrophilic chlorination of dihydroxy-2-methyl-4-oxo-indeno[1,2-b]pyrroles

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68378271%3A_____%2F23%3A00573800" target="_blank" >RIV/68378271:_____/23:00573800 - isvavai.cz</a>

Výsledek na webu

<a href="https://hdl.handle.net/11104/0344159" target="_blank" >https://hdl.handle.net/11104/0344159</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d3ra02515b" target="_blank" >10.1039/d3ra02515b</a>

Jazyk výsledku

angličtina

Název v původním jazyce

POCl3 mediated one-pot deoxygenative aromatization and electrophilic chlorination of dihydroxy-2-methyl-4-oxo-indeno[1,2-b]pyrroles

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

POCl3 mediated one-pot deoxygenative aromatization and electrophilic chlorination of dihydroxy-2-methyl-4-oxo-indeno[1,2-b]pyrroles

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10302 - Condensed matter physics (including formerly solid state physics, supercond.)

Projekt

<a href="/cs/project/LM2018096" target="_blank" >LM2018096: Laboratoř pro syntézu a měření materiálů</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

RSC Advances

ISSN

2046-2069

e-ISSN

2046-2069

Svazek periodika

13

Číslo periodika v rámci svazku

26

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

5

Strana od-do

17812-17816

Kód UT WoS článku

001007514000001

EID výsledku v databázi Scopus

2-s2.0-85162778648