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A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions.

ABSTRACT: A rapid and efficient one pot solvent/scavenger-free protocol for the synthesis of 2-iminothiazolidin-4-ones has been developed. Interestingly, the regio/stereoselective synthesis affords the regioisomeric (Z)-3-alkyl/aryl-2-(2-phenylcyclohex-2-enylimino)thiazolidin-4-one as the sole product in good yield. The selectivities observed have been rationalized based on the relative magnitude of the allylic strains developed during the course of the reaction. This is the first report wherein the impact of allylic strains in directing the regiocyclization has been noted.

SUBMITTER: Sathishkumar M

PROVIDER: S-EPMC3628849 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions.

Sathishkumar Murugan M Nagarajan Sangaraiah S Shanmugavelan Poovan P Dinesh Murugan M Ponnuswamy Alagusundaram A

Beilstein journal of organic chemistry 20130410

A rapid and efficient one pot solvent/scavenger-free protocol for the synthesis of 2-iminothiazolidin-4-ones has been developed. Interestingly, the regio/stereoselective synthesis affords the regioisomeric (Z)-3-alkyl/aryl-2-(2-phenylcyclohex-2-enylimino)thiazolidin-4-one as the sole product in good yield. The selectivities observed have been rationalized based on the relative magnitude of the allylic strains developed during the course of the reaction. This is the first report wherein the impac ...[more]

PMID: 23616814

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