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. Brambilla
Primo
Investigation
;
A. Gritti
Secondo
Investigation
;
V. Pirovano
Conceptualization
;
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.
Active DES; cyclization; dielectric heating; domino reactions; nitrogen heterocycles;
Settore CHIM/06 - Chimica Organica
apr-2023
20-mar-2023
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/959085
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