PREPARATION OF α-ACETYLOXY-N-CYCLOHEXYLAMIDES VIA PASSERINI REACTION USING DIMETHYLCARBONATE AS ECO-FRIENDLY SOLVENT

Author(s)

Bárbara R. Oliveira ^[1] ; Carla C. Silva ^[2] ; Juliana C. P. Calado ^[3] ; Wagner L. Batista ^[4] ; Fernanda A. Siqueira ^[5] ; Luiz S. Longo Jr. ^[6]

Affiliation

^[1] Universidade Federal de São Paulo. Instituto de Ciências Ambientais, Químicas e Farmacêuticas. Departamento de Ciências Farmacêuticas - Brasil

^[2] Universidade Federal de São Paulo. Instituto de Ciências Ambientais, Químicas e Farmacêuticas. Departamento de Ciências Farmacêuticas - Brasil

^[3] Universidade Federal de São Paulo. Instituto de Ciências Ambientais, Químicas e Farmacêuticas. Departamento de Ciências Farmacêuticas - Brasil

^[4] Universidade Federal de São Paulo. Instituto de Ciências Ambientais, Químicas e Farmacêuticas. Departamento de Ciências Farmacêuticas - Brasil

^[5] Universidade Federal de São Paulo. Instituto de Ciências Ambientais, Químicas e Farmacêuticas. Departamento de Química - Brasil

^[6] Universidade Federal de São Paulo. Instituto de Ciências Ambientais, Químicas e Farmacêuticas. Departamento de Ciências Farmacêuticas - Brasil

• Document type: Journal article
• Source: Química Nova; v. 41, n. 1, p. 92-99, 2018-01-00.

Abstract

A series of α-acetyloxy-N-cyclohexylamides was efficiently obtained via Passerini reaction of cyclohexyl isocyanide, acetic acid, and different aromatic and aliphatic aldehydes using refluxing dichloromethane or dimethylcarbonate (DMC). Reactions performed with DMC led to desired products in moderate to good yields, corroborating this solvent as a eco-friendly alternative to the chlorinated solvents commonly used in this transformation. The α-acetyloxy-N-cyclohexylamides thus obtained were tested against Escherichia coli, Bacillus cereus, Pseudomonas aeruginosa, and Staphylococcus aureus, as well as promastigote forms of L.(L.) amazonensis. The α-(Acetyloxy)-N-cyclohexyl-pentanamide showed low antibacterial activity against Gram-positive (S. aureus and B. cereus) and Gram negative (E. coli and P. aeruginosa) bacteria (MIC = 8,3-16,5 mmol L-1), while α-(acetyloxy)-N-cyclohexyl-4-bromo-benzeneacetamide showed leishmanicidal activitity (IC50 = 0,099 mmol L-1). (AU)

• FAPESP's process: 07/07338-6 - Studies towards the synthesis of decalactones
• Grantee: Luiz Sidney Longo Junior
• Support type: Research Grants - Young Investigators Grants
• FAPESP's process: 11/12821-3 - Dynamic kinetic resolution of amines and synthesis of molecules with remarkable biological activity
• Grantee: Fernanda Amaral de Siqueira
• Support type: Regular Research Grants