Ammonium Chloride Promoted Three-Component Synthesis of 5-Iminooxazoline and Its Subsequent Transformation to Macrocyclodepsipeptide
2007
Abstract
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)]
Details
Title
Ammonium Chloride Promoted Three-Component Synthesis of 5-Iminooxazoline and Its Subsequent Transformation to Macrocyclodepsipeptide
Author(s)
Pirali, Tracey ; Tron, Gian Cesare ; Masson, Geraldine ; Zhu, Jieping
Published in
Organic Letters
Volume
9
Issue
25
Pages
5275-5278
Date
2007
ISSN
1523-7060
Keywords
Alcohols Role: RCT (Reactant); RACT (Reactant or reagent) (amino; prepn. of iminooxazolines via ammonium chloride-promoted three-component reaction of isocyanoacetamides; aldehydes and amino alcs.); Peptides Role: SPN (Synthetic preparation); PREP (Preparation) (depsipeptides; macrocyclic; prepn. of macrocyclodepsipeptides via cyclization of iminooxazolines); Aldehydes Role: RCT (Reactant); RACT (Reactant or reagent) (prepn. of iminooxazolines via ammonium chloride-promoted three-component reaction of isocyanoacetamides; aldehydes and amino alcs.); Ugi reaction (prepn. of isocyanoacetamides via Ugi reaction of ketones; ammonium formate and isocyanoacetates); Ketones Role: RCT (Reactant); RACT (Reactant or reagent) (prepn. of isocyanoacetamides via Ugi reaction of ketones; ammonium formate and isocyanoacetates); Cyclization (prepn. of macrocyclodepsipeptides via cyclization of iminooxazolines); Macrocyclic compounds Role: SPN (Synthetic preparation); PREP (Preparation) (prepn. of macrocyclodepsipeptides via cyclization of iminooxazolines); Multicomponent reaction (three-component; prepn. of iminooxazolines via ammonium chloride-promoted three-component reaction of isocyanoacetamides; aldehydes and amino alcs.); iminooxazoline prepn three component reaction isocyanoacetamide aldehyde amino alc; macrocyclodepsipeptide prepn iminooxazoline sapon cyclization
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
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)
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
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
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25