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LiAlH4-induced thia-aza-Payne rearrangement of functionalized 2-(thiocyanatomethyl)aziridines into 2-(aminomethyl)thiiranes as an entry to 5-(chloromethyl)thiazolidin-2-ones

Jeroen Dolfen (UGent) , Kristof Van Hecke (UGent) and Matthias D'hooghe (UGent)
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Abstract
Nonactivated 2-(thiocyanatomethyl)aziridines with diverse substitution patterns were deployed as substrates to effect a LiAlH4-promoted thia-aza-Payne rearrangement to provide access to functionalized 2-(aminomethyl) thiiranes in good to excellent yields (78-94 %). The developed strategy involved hydride reduction of the thiocyanato moiety followed by intramolecular aziridine ring opening. Subsequent exposure of the obtained 2-(aminomethyl) episulfide intermediates to triphosgene resulted in the formation of 5-(chloromethyl)thiazolidin-2-ones.
Keywords
Heterocycles, Rearrangement, Reduction, Regioselectivity, Small ring systems, BUILDING-BLOCKS, AZIRIDINES, ALCOHOLS, TRANSFORMATION, SUBSTITUENTS, HETEROCYCLES, THIIRANES, TAURINES, CARBON, ALPHA

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Chicago
Dolfen, Jeroen, Kristof Van Hecke, and Matthias D’hooghe. 2017. “LiAlH4-induced thia-aza-Payne Rearrangement of Functionalized 2-(thiocyanatomethyl)aziridines into 2-(aminomethyl)thiiranes as an Entry to 5-(chloromethyl)thiazolidin-2-ones.” European Journal of Organic Chemistry (22): 3229–3233.
APA
Dolfen, J., Van Hecke, K., & D’hooghe, M. (2017). LiAlH4-induced thia-aza-Payne rearrangement of functionalized 2-(thiocyanatomethyl)aziridines into 2-(aminomethyl)thiiranes as an entry to 5-(chloromethyl)thiazolidin-2-ones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (22), 3229–3233.
Vancouver
1.
Dolfen J, Van Hecke K, D’hooghe M. LiAlH4-induced thia-aza-Payne rearrangement of functionalized 2-(thiocyanatomethyl)aziridines into 2-(aminomethyl)thiiranes as an entry to 5-(chloromethyl)thiazolidin-2-ones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2017;(22):3229–33.
MLA
Dolfen, Jeroen, Kristof Van Hecke, and Matthias D’hooghe. “LiAlH4-induced thia-aza-Payne Rearrangement of Functionalized 2-(thiocyanatomethyl)aziridines into 2-(aminomethyl)thiiranes as an Entry to 5-(chloromethyl)thiazolidin-2-ones.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 22 (2017): 3229–3233. Print.
@article{8541564,
  abstract     = {Nonactivated 2-(thiocyanatomethyl)aziridines with diverse substitution patterns were deployed as substrates to effect a LiAlH4-promoted thia-aza-Payne rearrangement to provide access to functionalized 2-(aminomethyl) thiiranes in good to excellent yields (78-94 %). The developed strategy involved hydride reduction of the thiocyanato moiety followed by intramolecular aziridine ring opening. Subsequent exposure of the obtained 2-(aminomethyl) episulfide intermediates to triphosgene resulted in the formation of 5-(chloromethyl)thiazolidin-2-ones.},
  author       = {Dolfen, Jeroen and Van Hecke, Kristof and D'hooghe, Matthias},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {Heterocycles,Rearrangement,Reduction,Regioselectivity,Small ring systems,BUILDING-BLOCKS,AZIRIDINES,ALCOHOLS,TRANSFORMATION,SUBSTITUENTS,HETEROCYCLES,THIIRANES,TAURINES,CARBON,ALPHA},
  language     = {eng},
  number       = {22},
  pages        = {3229--3233},
  title        = {LiAlH4-induced thia-aza-Payne rearrangement of functionalized 2-(thiocyanatomethyl)aziridines into 2-(aminomethyl)thiiranes as an entry to 5-(chloromethyl)thiazolidin-2-ones},
  url          = {http://dx.doi.org/10.1002/ejoc.201700549},
  year         = {2017},
}

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