We describe an alternative and more sustainable method for the synthesis of 2,2′-disubstituted 3,3′‑biindoles starting from 2,2’-diaminotolanes and (hetero)arylaldehydes. The key feature of the approach is the use of an acidic DES able to exploit a double activity, i.e. solvent and BA catalyst, avoiding the use of VOCs as solvents and additional acid catalysts. By this way, we synthesized twenty-five biindoles, including eighteen new compounds. The reactions run quickly under mild conditions by microwave heating at 70 °C, with yields ranging from good to very good. The reaction scope is rather broad. The medium demonstrated to be reusable at least five times with only a slight reduction in yields. Based on experimental evidence and previous literature findings, a plausible mechanism is proposed.
Acidic DESs as Active Media for a Sustainable Synthesis of Biindoles Starting from 2,2’‐Diaminotolanes and Aldehydes / E. Brambilla, A. Gritti, V. Pirovano, A. Arcadi, R. Germani, M. Tiecco, G. Abbiati. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 26:16(2023 Apr), pp. e202300204.1-e202300204.11. [10.1002/ejoc.202300204]
Acidic DESs as Active Media for a Sustainable Synthesis of Biindoles Starting from 2,2’‐Diaminotolanes and Aldehydes
E. BrambillaPrimo
Investigation
;A. GrittiSecondo
Investigation
;V. PirovanoConceptualization
;G. Abbiati
Ultimo
Conceptualization
2023
Abstract
We describe an alternative and more sustainable method for the synthesis of 2,2′-disubstituted 3,3′‑biindoles starting from 2,2’-diaminotolanes and (hetero)arylaldehydes. The key feature of the approach is the use of an acidic DES able to exploit a double activity, i.e. solvent and BA catalyst, avoiding the use of VOCs as solvents and additional acid catalysts. By this way, we synthesized twenty-five biindoles, including eighteen new compounds. The reactions run quickly under mild conditions by microwave heating at 70 °C, with yields ranging from good to very good. The reaction scope is rather broad. The medium demonstrated to be reusable at least five times with only a slight reduction in yields. Based on experimental evidence and previous literature findings, a plausible mechanism is proposed.File | Dimensione | Formato | |
---|---|---|---|
Supporting_Information_Abbiati_Biindoles_DES.pdf
accesso aperto
Descrizione: Supporting Information
Tipologia:
Altro
Dimensione
1.9 MB
Formato
Adobe PDF
|
1.9 MB | Adobe PDF | Visualizza/Apri |
Reprint.pdf
accesso aperto
Tipologia:
Publisher's version/PDF
Dimensione
2.88 MB
Formato
Adobe PDF
|
2.88 MB | Adobe PDF | Visualizza/Apri |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.