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

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

Pirali, Tracey
•
Tron, Gian Cesare
•
Masson, Geraldine
Show more
2007
Organic Letters

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
  • Metrics
Type
research article
DOI
10.1021/ol7024372
Author(s)
Pirali, Tracey
•
Tron, Gian Cesare
•
Masson, Geraldine
•
Zhu, Jieping  
Date Issued

2007

Published in
Organic Letters
Volume

9

Issue

25

Start page

5275

End page

5278

Subjects

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58429
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