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A Straightforward Synthesis of 4,7-Disubstituted 1,4-Oxazepanes via a Brønsted Acid-Catalyzed Intramolecular Etherification Reaction

Author(s):

Juan-Carlos Castillo, Jaime Portilla, Braulio Insuasty, Jairo Quiroga and Rodrigo Abonia*  

Abstract:


Based on an intramolecular etherification strategy, a three-component Mannich-type approach was implemented for the synthesis of novel 4,7-disubstituted 1,4-oxazepanes in moderate yields by treatment of ethanolamines with polyformaldehyde and N-vinylpyrrolidin-2-one in ACN as solvent at room temperature. Alternatively, through a careful temperature control, analog structures were selectively obtained in acceptable to good yields from a H2SO4 catalyzed intramolecular etherification reaction of diversely substituted N-tethered bis-alcohols in p-dioxane as solvent. According to the results, etherification reactions proceeded with the formation of benzylic carbocations as the key intermediates for the generation of the title compounds.

Keywords:

Etherification reaction, N-tethered bis-alcohols, Mannich-type reaction, 1, 4-oxazepanes, intramolecular cyclization

Affiliation:

Research Group of Heterocyclic Compounds, Department of Chemistry, Universidad del Valle, A. A. 25360, Cali, Bioorganic Compounds Research Group, Department of Chemistry, Universidad de los Andes, Bogotá 111711, Research Group of Heterocyclic Compounds, Department of Chemistry, Universidad del Valle, A. A. 25360, Cali, Research Group of Heterocyclic Compounds, Department of Chemistry, Universidad del Valle, A. A. 25360, Cali, Research Group of Heterocyclic Compounds, Department of Chemistry, Universidad del Valle, A. A. 25360, Cali



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