An efficient and expeditious synthesis of di- and trisubstituted amino-phenyl and -benzyl derivatives of tetrazole and [1,3,4]oxadiazol-2-one.
A practical protocol for the parallel synthesis and purification of amino tetrazole and [1,3,4]oxadiazol-2-one derivatives as carboxylic acid bioisosteres is described. Phenyl- and benzyl-amines, substituted with tetrazole or [1,3,4]oxadiazol-2-one, were transformed into functionally diverse and novel compounds, with p K a values ranging from 4.9 to 8.4, by two sequential reductive alkylation reactions. These series of di- and trisubstituted amino-phenyl and -benzyl derivatives were produced in solution using solid-supported reagents and were purified by solid-phase extraction (SPE) techniques.
Desforges
Gwenaelle
G
Merck Serono Geneva Research Center, 9 Chemin des Mines, CH-1202 Geneva, Switzerland.
Bombrun
Agnes
A
Quattropani
Anna
A
D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D004952:Esters / Q000737:chemistry; D008956:Models, Chemical; D010069:Oxadiazoles / Q000138:chemical synthesis*; D052616:Solid Phase Extraction; D013777:Tetrazoles / Q000138:chemical synthesis*
D000588:Amines; D001555:Benzene Derivatives; D002264:Carboxylic Acids; D004952:Esters; D010069:Oxadiazoles; D013777:Tetrazoles