Amphoteric 2-(sulfonylamino)benzaldehydes, secondary amines and isocyanides in the multicomponent synthesis of elusive N-alkyl-2, 3-diaminoindoles. Issue 45 (8th November 2017)

• Record Type: Journal Article
• Authors: Giustiniano, Mariateresa; Pelliccia, Sveva; Sangaletti, Luca; Meneghetti, Fiorella; Amato, Jussara; Novellino, Ettore; Tron, Gian Cesare
• Is Part Of: Tetrahedron letters. Volume 58:Issue 45(2017)
• Page Start: 4264
• Page End: 4268
• Publication Date: 2017-11-08
• Subjects: Multicomponent reactions -- 2-(Sulfonylamino)benzaldehyde -- Isocyanides -- Secondary amines -- N-alkyl 2 -- 3-Diaminoindoles; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.09.076
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: One pot synthesis of N -alkyl 2, 3-diaminoindoles. The sulphonamide group intercepts the nascent nitrilium ion. No transition metals required. 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.