Acidic Deep Eutectic Solvents as Active Media for Sustainable Synthesis of Biindoles Starting from 2,2’‐Diaminotolanes and Aldehydes

Author:

Brambilla Elisa1ORCID,Gritti Alessandra1,Pirovano Valentina1ORCID,Arcadi Antonio2ORCID,Germani Raimondo3ORCID,Tiecco Matteo4ORCID,Abbiati Giorgio1ORCID

Affiliation:

1. Dipartimento di Scienze Farmaceutiche Sezione di Chimica Generale e Organica “A. Marchesini” Università degli Studi di Milano Via Golgi 19 20133 Milano Italy

2. Dipartimento di Ingegneria e Scienze dell'Informazione e Matematica Università degli Studi dell'Aquila Via Vetoio 67010 Coppito L'Aquila (Italia

3. Dipartimento di Chimica, Biologia e Biotecnologie Università di Perugia Via Elce di Sotto 8 06123 Perugia Italia

4. Chemistry Interdisciplinary Project (ChIP) Scuola di Scienze del Farmaco e dei Prodotti della Salute Università di Camerino via Madonna delle Carceri 62032 Camerino MC Italia

Abstract

AbstractWe 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 Deep Eutectic Solvent (DES) able to exploit a double activity, i. e., solvent and Brønsted Acid (BA) catalyst, avoiding the use of Volatile Organic Compounds (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.

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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