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

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...

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Autores principales: Sathishkumar, Murugan, Nagarajan, Sangaraiah, Shanmugavelan, Poovan, Dinesh, Murugan, Ponnuswamy, Alagusundaram
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3628849/
https://www.ncbi.nlm.nih.gov/pubmed/23616814
http://dx.doi.org/10.3762/bjoc.9.78
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author Sathishkumar, Murugan
Nagarajan, Sangaraiah
Shanmugavelan, Poovan
Dinesh, Murugan
Ponnuswamy, Alagusundaram
author_facet Sathishkumar, Murugan
Nagarajan, Sangaraiah
Shanmugavelan, Poovan
Dinesh, Murugan
Ponnuswamy, Alagusundaram
author_sort Sathishkumar, Murugan
collection PubMed
description 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.
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spelling pubmed-36288492013-04-24 A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions Sathishkumar, Murugan Nagarajan, Sangaraiah Shanmugavelan, Poovan Dinesh, Murugan Ponnuswamy, Alagusundaram Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2013-04-10 /pmc/articles/PMC3628849/ /pubmed/23616814 http://dx.doi.org/10.3762/bjoc.9.78 Text en Copyright © 2013, Sathishkumar et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Sathishkumar, Murugan
Nagarajan, Sangaraiah
Shanmugavelan, Poovan
Dinesh, Murugan
Ponnuswamy, Alagusundaram
A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions
title A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions
title_full A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions
title_fullStr A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions
title_full_unstemmed A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions
title_short A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions
title_sort facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3628849/
https://www.ncbi.nlm.nih.gov/pubmed/23616814
http://dx.doi.org/10.3762/bjoc.9.78
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