Efficient Synthesis of alpha -Ketoamides via 2-Acyl-5-aminooxazoles by Reacting Acyl Chlorides and alpha -Isocyanoacetamides

Acyl chlorides R1COCl [R1 = Et, n-pentyl, PhCH2CH2, 2-cyclopentylethyl, (S)-PhCHEt] efficiently reacted with alpha -isocyanoacetamides R2R3NCOCH(NC)R4 (R2 = H, R3 = n-Bu, PhCH2, HC==CCH2; R2 = Me, R3 = HC==CCH2, PhCH2; R2R3N = 4-morpholinyl; R4 = H, Me, PhCH2) in dichloromethane in the presence of triethylamine to give 2-acyl-5-aminooxazoles I. Subsequent acid hydrolysis of the 5-aminooxazole moiety leads to alpha -ketoamides II in good overall yields. [on SciFinder (R)]


Published in:
Organic Letters, 12, 4, 820-823
Year:
2010
Keywords:
Note:
CAN 152:238828, 28-6, Heterocyclic Compounds (More Than One Hetero Atom), Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche,Universita degli Studi del Piemonte Orientale "A. Avogadro",Novara,Italy., Journal, 1523-7060, written in English., 1207525-75-4P Role: BYP (Byproduct), PREP (Preparation) (efficient synthesis of alpha -ketoamides via cyclocondensation of acyl chlorides with alpha -isocyano amides followed by hydrolysis/ring opening of 2-acyl-5-aminooxazoles); 79-03-8 (Propanoyl chloride); 100-46-9 (Benzylamine); 103-67-3 (Benzyl methyl amine); 104-97-2 (3-(Cyclopentyl)propanoyl chloride); 109-73-9 (n-Butylamine); 142-61-0 (Hexanoyl chloride); 645-45-4 (Hydrocinnamoyl chloride); 39687-95-1 (Methyl isocyanoacetate); 40473-35-6; 85059-48-9; 911306-04-2; 1207525-77-6 Role: RCT (Reactant), RACT (Reactant or reagent) (efficient synthesis of alpha -ketoamides via cyclocondensation of acyl chlorides with alpha -isocyano amides followed by hydrolysis/ring opening of 2-acyl-5-aminooxazoles); 63348-60-7P; 74900-84-8P; 1207525-74-3P; 1207525-78-7P; 1207525-79-8P; 1207525-80-1P; 1207525-81-2P; 1207525-82-3P; 1207525-83-4P; 1207525-84-5P; 1207525-85-6P; 1207525-86-7P; 1207525-87-8P; 1207525-88-9P; 1207525-89-0P; 1207525-90-3P; 1207525-91-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (efficient synthesis of alpha -ketoamides via cyclocondensation of acyl chlorides with alpha -isocyano amides followed by hydrolysis/ring opening of 2-acyl-5-aminooxazoles); 1207525-76-5P; 1207525-92-5P; 1207525-93-6P; 1207525-94-7P; 1207525-96-9P; 1207525-97-0P; 1207525-98-1P; 1207525-99-2P; 1207526-00-8P; 1207526-01-9P; 1207526-02-0P; 1207526-03-1P; 1207526-04-2P Role: SPN (Synthetic preparation), PREP (Preparation) (efficient synthesis of alpha -ketoamides via cyclocondensation of acyl chlorides with alpha -isocyano amides followed by hydrolysis/ring opening of 2-acyl-5-aminooxazoles)
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 Record created 2010-11-25, last modified 2018-01-28


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