Rh(III)-Catalyzed C-2 Alkylation of Indoles followed by a Post-Synthetic Modification via the Ugi Reaction

Author(s)

Januario, Marcelo Augusto Pereira ; de Souza, Demetrius P. ; Zukerman-Schpector, Julio ; Correa, Arlene G.

• Document type: Journal article
• Source: CHEMISTRYOPEN; v. 12, n. 6, p. 8-pg., 2023-06-01.

Abstract

Indole derivatives substituted at the C-2 position have shown important biological activities. Due to these properties, several methods have been described for the preparation of structurally diverse indoles. In this work, we have synthesized highly functionalized indole derivatives via Rh(III)-catalyzed C-2 alkylation with nitroolefins. Under the optimized condition, 23 examples were prepared with 39-80 % yield. Moreover, the nitro compounds were reduced and submitted to the Ugi four-component reaction, furnishing a series of new indole-peptidomimetics in moderate to good overall yields. (AU)

• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 21/12394-0 - Sustainable synthetic methods employing catalysis, benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 14/50918-7 - INCT 2014: for the Biorational Control of Pest-Insect and Phytopathogens
• Grantee: Maria Fátima das Graças Fernandes da Silva
• Support Opportunities: Research Projects - Thematic Grants