Reeve's synthesis of 2-imino-4-thiazolidinone from alkyl (aryl) trichloromethylcarbinol revisited, a three-component process from aldehyde, chloroform, and thiourea
2004
Abstract
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)]
Details
Title
Reeve's synthesis of 2-imino-4-thiazolidinone from alkyl (aryl) trichloromethylcarbinol revisited, a three-component process from aldehyde, chloroform, and thiourea
Author(s)
Blanchet, Jerome ; Zhu, Jieping
Published in
Tetrahedron Letters
Volume
45
Issue
23
Pages
4449-4452
Date
2004
ISSN
0040-4039
Keywords
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)
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)
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