One-pot synthesis of N-substituted pantolactams from pantolactone
Rac-N-substituted pantolactams (5) are readily obtained in medium to good yields by reaction of rac-pantolactone (1) with primary amines under acid catalysis, whether at 250°C in a pressure reactor or under microwave irradiation. It appears that the amine can react with pantolactone at the carbonyl carbon atom to give a hydroxyamide (3) in a reversible way and at the methylene carbon atom to give a γ-amino acid (4). The last one on dehydration would give the corresponding pantolactam (5).
Barrios, Ivana,Camps, Pelayo,Comes-Franchini, Mauro,Mu?oz-Torrero, Diego,Ricci, Alfredo,Sánchez, Laura
p. 1971 - 1979
(2007/10/03)
A convenient dehydration procedure for the synthesis of enantiomerically pure cyanohydrins
Starting from protected α-hydroxy amides; cyanohydrins (α-hydroxy nitriles) are obtained through dehydration by cyanuric chloride/DMF in excellent yield. The advantages of the procedure are the extremely mild reaction conditions that prevent racemization.
Aquino, Fabrice,Pauling, Horst,Walther, Willy,Plattner, Dietmar A.,Bonrath, Werner
p. 731 - 737
(2007/10/03)
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