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.
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 degrees 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.
Machetti
Fabrizio
F
Istituto di chimica dei composti organometallici del CNR c/o Dipartimento di chimica organica Ugo Schiff, Università degli Studi di Firenze, Firenze, Italy. fabrizio.machetti@unifi.it
Bucelli
Ilaria
I
Indiani
Giovanni
G
Kappe
C Oliver
CO
Guarna
Antonio
A
D000577:Amides / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000577:Amides; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004952:Esters