A novel interrupted Ugi reaction between ortho-sulfonylaminated aryl aldehydes, secondary amines, and isocyanides affords in good to high yields N-alkyl-2,3-diaminoindoles, providing access to a so far unexplored area of the indole chemical space. With only one single chemical operation, this novel reaction affords a broad gamma of substituted 2,3-diaminoindoles with five points of diversity. The success of this novel multicomponent transformation lies in presence of the amphoteric sulfonylamino group, which sequentially acts as a Brønsted acids and as a nucleophile the lack of need for additional catalysts and the high atom economy, with the loss of only one molecule of water, renders this approach a very effective one.

Amphoteric 2-(sulfonylamino) benzaldehydes, secondary amines and isocyanides in the multicomponent synthesis of elusive N-alkyl-2,3-diaminoindoles / M. Giustiniano, S. Pelliccia, L. Sangaletti, F. Meneghetti, J. Amato, E. Novellino, G.C. Tron. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 58:45(2017 Nov 08), pp. 4264-4268. [10.1016/j.tetlet.2017.09.076]

Amphoteric 2-(sulfonylamino) benzaldehydes, secondary amines and isocyanides in the multicomponent synthesis of elusive N-alkyl-2,3-diaminoindoles

F. Meneghetti;
2017-11-08

Abstract

A novel interrupted Ugi reaction between ortho-sulfonylaminated aryl aldehydes, secondary amines, and isocyanides affords in good to high yields N-alkyl-2,3-diaminoindoles, providing access to a so far unexplored area of the indole chemical space. With only one single chemical operation, this novel reaction affords a broad gamma of substituted 2,3-diaminoindoles with five points of diversity. The success of this novel multicomponent transformation lies in presence of the amphoteric sulfonylamino group, which sequentially acts as a Brønsted acids and as a nucleophile the lack of need for additional catalysts and the high atom economy, with the loss of only one molecule of water, renders this approach a very effective one.
2-(Sulfonylamino)benzaldehyde; 3-Diaminoindoles; Isocyanides; Multicomponent reactions; N-alkyl 2; Secondary amines; Biochemistry; Drug Discovery; 3003; Pharmaceutical Science; Organic Chemistry
Settore CHIM/08 - Chimica Farmaceutica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/528408
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