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Three-component, one-flask synthesis of rhodanines (thiazolidinones).

ABSTRACT: 5-(Z)-alkylidene-2-thioxo-1,3-thiazolidin-4-ones (rhodanine derivatives) were prepared by reaction of in situ generated dithiocarbamates with recently reported racemic ?-chloro-?,?-alkenoate esters. This multicomponent sequential transformation performed in one reaction flask represents a general route to this medicinally valuable class of sulfur/nitrogen heterocycles. Using this convergent procedure, we prepared an analogue of the drug epalrestat, an aldose reductase inhibitory rhodanine.

SUBMITTER: Jacobine AM 

PROVIDER: S-EPMC3184363 | biostudies-other | 2011 Oct

REPOSITORIES: biostudies-other

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Three-component, one-flask synthesis of rhodanines (thiazolidinones).

Jacobine Alexander M AM   Posner Gary H GH  

The Journal of organic chemistry 20110831 19

5-(Z)-alkylidene-2-thioxo-1,3-thiazolidin-4-ones (rhodanine derivatives) were prepared by reaction of in situ generated dithiocarbamates with recently reported racemic α-chloro-β,γ-alkenoate esters. This multicomponent sequential transformation performed in one reaction flask represents a general route to this medicinally valuable class of sulfur/nitrogen heterocycles. Using this convergent procedure, we prepared an analogue of the drug epalrestat, an aldose reductase inhibitory rhodanine. ...[more]