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

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)]


Published in:
Tetrahedron Letters, 45, 23, 4449-4452
Year:
2004
Keywords:
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
0040-4039
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:




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


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