Ammonium Chloride Promoted Three-Component Synthesis of 5-Iminooxazoline and Its Subsequent Transformation to Macrocyclodepsipeptide

A three-component reaction of an alpha ,alpha -disubstituted alpha -isocyanoacetamide, an aldehyde and an amino alc. afforded 5-iminooxazolines, which, upon sapon., cyclized under acidic conditions to provide the macrocyclodepsipeptides in good overall yields. [on SciFinder (R)]


Published in:
Organic Letters, 9, 25, 5275-5278
Year:
2007
Keywords:
Note:
CAN 148:121943
34-3
Amino Acids, Peptides, and Proteins
Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche and Drug and Food Biotechnology Center,Universita degli Studi del Piemonte Orientale A. Avogadro,Novara,Italy.
Journal
1523-7060
written in English.
1000886-16-7P Role: SPN (Synthetic preparation), PREP (Preparation) (acidic hydrolysis of iminooxazolines); 110-91-8 (Morpholine); 111-71-7 (n-Heptanal); 702-24-9; 18545-16-9; 59578-63-1; 98648-05-6; 357277-74-8; 1000886-18-9 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of iminooxazolines via ammonium chloride-promoted three-component reaction of isocyanoacetamides, aldehydes and amino alcs.); 1000885-96-0P; 1000885-97-1P; 1000885-98-2P; 1000885-99-3P; 1000886-00-9P; 1000886-01-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of iminooxazolines via ammonium chloride-promoted three-component reaction of isocyanoacetamides, aldehydes and amino alcs.); 1000886-15-6P; 1000886-17-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of iminooxazolines via ammonium chloride-promoted three-component reaction of isocyanoacetamides, aldehydes and amino alcs.); 62-57-7 (alpha -Aminoisobutyric acid); 67-64-1 (Acetone); 78-84-2; 108-94-1 (Cyclohexanone); 120-92-3 (Cyclopentanone); 122-78-1 (Benzeneacetaldehyde); 540-69-2 (Ammonium formate); 2043-61-0 (Cyclohexanecarboxaldehyde); 39687-95-1; 71015-20-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of isocyanoacetamides via Ugi reaction of ketones, ammonium formate and isocyanoacetates); 76539-57-6P; 1000885-92-6P; 1000885-93-7P; 1000885-94-8P; 1000885-95-9P; 1000886-12-3P; 1000886-13-4P; 1000886-14-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of isocyanoacetamides via Ugi reaction of ketones, ammonium formate and isocyanoacetates); 133437-08-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of macrocyclodepsipeptides via cyclization of iminooxazolines); 1000886-02-1P; 1000886-03-2P; 1000886-04-3P; 1000886-05-4P; 1000886-06-5P; 1000886-07-6P; 1000886-08-7P; 1000886-09-8P; 1000886-10-1P; 1000886-11-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of macrocyclodepsipeptides via cyclization of iminooxazolines)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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