research article

Reeve's synthesis of 2-imino-4-thiazolidinone from alkyl (aryl) trichloromethylcarbinol revisited, a three-component process from aldehyde, chloroform, and thiourea

Blanchet, Jerome
•
Zhu, Jieping  
2004
Tetrahedron Letters

An efficient synthesis of 2-imino-4-thiazolidinones from readily accessible alkyl or aryl trichloromethylcarbinols with thioureas, under mild conditions, is reported. A one-pot three-component synthesis of the title compds. from aldehyde, chloroform and thiourea was also developed. [on SciFinder (R)]

Type
research article
DOI
10.1016/j.tetlet.2004.04.055
Author(s)
Blanchet, Jerome
•
Zhu, Jieping  
Date Issued

2004

Publisher

Elsevier

Published in
Tetrahedron Letters
Volume

45

Issue

23

Start page

4449

End page

4452

Subjects

Heterocyclization (Reeve's reaction; prepn. of iminothiazolidinones via nucleophilic addn. of chloroform to aldehydes followed by Reeve's reaction with thioureas); Aldehydes Role: RCT (Reactant)

•

RACT (Reactant or reagent) (prepn. of iminothiazolidinones via nucleophilic addn. of chloroform to aldehydes followed by Reeve's reaction with thioureas); Alcohols Role: RCT (Reactant)

•

SPN (Synthetic preparation)

•

PREP (Preparation)

•

RACT (Reactant or reagent) (prepn. of iminothiazolidinones via nucleophilic addn. of chloroform to aldehydes followed by Reeve's reaction with thioureas); Coupling reaction (three-component; prepn. of iminothiazolidinones via nucleophilic addn. of chloroform to aldehydes followed by Reeve's reaction with thioureas)

•

aldehyde chloroform nucleophilic addn; chloromethylcarbinol prepn thiourea Reeve synthesis; iminothiazolidinone prepn Reeve synthesis

Note

CAN 141:89029

28-7

Heterocyclic Compounds (More Than One Hetero Atom)

Institut de Chimie des Substances Naturelles CNRS,Gif-sur-Yvette,Fr.

Journal

written in English.

62-53-3 (Benzenamine); 62-56-6 (Thiourea); 66-77-3 (1-Naphthylaldehyde); 67-66-3 (Chloroform); 78-84-2 (Isobutanal); 100-52-7 (Benzaldehyde); 103-85-5 (Phenylthiourea); 106-40-1; 106-95-6 (Allylbromide); 122-03-2 (p-Isopropylbenzaldehyde); 122-78-1 (Phenylacetaldehyde); 124-13-0 (Octanal); 333-20-0; 387-45-1 (2-Chloro-6-fluorobenzaldehyde); 456-48-4 (m-Fluorobenzaldehyde); 459-57-4 (p-Fluorobenzaldehyde); 2043-61-0 (Cyclohexanecarboxaldehyde); 2646-30-2 (p-Bromophenylthiourea) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of iminothiazolidinones via nucleophilic addn. of chloroform to aldehydes followed by Reeve's reaction with thioureas); 394-56-9P; 2000-43-3P; 4776-43-6P; 6111-11-1P; 19126-05-7P; 32766-45-3P; 55011-04-6P; 57741-12-5P; 74592-82-8P; 716316-05-1P; 716316-06-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of iminothiazolidinones via nucleophilic addn. of chloroform to aldehydes followed by Reeve's reaction with thioureas); 1762-68-1P; 3805-17-2P; 21261-54-1P; 36387-87-8P; 50871-26-6P; 50871-27-7P; 215933-00-9P; 716316-07-3P; 716316-08-4P; 716316-09-5P; 716316-10-8P; 716316-11-9P; 716316-12-0P; 716316-13-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of iminothiazolidinones via nucleophilic addn. of chloroform to aldehydes followed by Reeve's reaction with thioureas)

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/20.500.14299/58485