Synthesis of 1,2,5-substituted pyrrole derivatives by a modification of the Reisch-Schulte reaction
Por:
Almaraz-Girón M.A., Aguilar-Lugo C., Vázquez-Hernández G.A., Fomine S., Salcedo R., Alexandrova L., Fomina L.
Publicada:
1 ene 2024
Ahead of Print:
1 dic 2023
Resumen:
A synthesis method was developed for the formation of several 1,2,5-substituted pyrrole derivatives and were characterized by NMR, IR, UV–Vis spectroscopies and HRMS. This method involves adding aniline derivatives to a dialkyne, catalyzed by Cu(I) and is carried out under modified Reisch-Schulte protocol by adding N,N,N',N'-tetramethylethylenediamine (TMEDA). Notably, the reaction does not proceed in absence of TMEDA. The yields of synthesized pyrroles ranged from quantitative to acceptable ones. Generally, the reaction yields correlated well with the Global nucleophilicities (GN) of the aniline reagents obtained from theoretical calculations; more nucleophilic anilines resulted in higher yields, except para-anisidine, the molecule with the biggest GN value. Mechanistic explications of the observed effects were proposed. Additionally, experimental studies and theoretical simulation showed that the novel pyrrole molecules had semiconducting properties since their band gap energy (Eg) lied within the range typical for organic semiconductors. It was observed that the presence of electron-withdrawing groups led to a significant decrease in the Eg value. © 2023 Elsevier B.V.
Filiaciones:
Almaraz-Girón M.A.:
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Ciudad Universitaria Coyoacán, Circuito exterior s/n, Ciudad de México, 04510, Mexico
Aguilar-Lugo C.:
Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria Coyoacán, Circuito exterior s/n, Ciudad de México, 04510, Mexico
Vázquez-Hernández G.A.:
Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria Coyoacán, Circuito exterior s/n, Ciudad de México, 04510, Mexico
Fomine S.:
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Ciudad Universitaria Coyoacán, Circuito exterior s/n, Ciudad de México, 04510, Mexico
Salcedo R.:
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Ciudad Universitaria Coyoacán, Circuito exterior s/n, Ciudad de México, 04510, Mexico
Alexandrova L.:
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Ciudad Universitaria Coyoacán, Circuito exterior s/n, Ciudad de México, 04510, Mexico
Fomina L.:
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Ciudad Universitaria Coyoacán, Circuito exterior s/n, Ciudad de México, 04510, Mexico
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