An efficient synthesis of unsubstituted and substituted amides based on the 6,8-dioxa-3-azabicyclo[3.2.1]octane scaffold is described. The reaction, carried out at 60 °C in the absence of solvent, is characterized by its mildness and ease of workup. A library of amides, was synthesized by combination of methyl esters 1−6 with various amines. In addition, the microwave-assisted automated synthesis of the library was compared with the above conventional parallel synthesis. Microwave synthesis significantly decreased the reaction time from hours to minutes.
Parallel Synthesis of an Amide Library Based on the 6,8-Dioxa-3-azabicyclo[3.2.1]octane Scaffold by Direct Aminolysis of Methyl Esters / F.Machetti; I.Bucelli; G.Indiani; O.Kappe; A.Guarna. - In: JOURNAL OF COMBINATORIAL CHEMISTRY. - ISSN 1520-4766. - STAMPA. - 9:(2007), pp. 454-461. [10.1021/cc060120o]
Parallel Synthesis of an Amide Library Based on the 6,8-Dioxa-3-azabicyclo[3.2.1]octane Scaffold by Direct Aminolysis of Methyl Esters.
MACHETTI, FABRIZIO;GUARNA, ANTONIO
2007
Abstract
An efficient synthesis of unsubstituted and substituted amides based on the 6,8-dioxa-3-azabicyclo[3.2.1]octane scaffold is described. The reaction, carried out at 60 °C in the absence of solvent, is characterized by its mildness and ease of workup. A library of amides, was synthesized by combination of methyl esters 1−6 with various amines. In addition, the microwave-assisted automated synthesis of the library was compared with the above conventional parallel synthesis. Microwave synthesis significantly decreased the reaction time from hours to minutes.
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