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Original Articles

Synthesis of Enantiopure Bis-Heterocycles Derived from (S)-Prolinehydrazides

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Pages 493-495 | Received 30 Sep 2012, Accepted 08 Oct 2012, Published online: 29 May 2013
 

Abstract

A convenient synthesis of new enantiomerically pure bis-heterocycles containing a (S)-proline moiety starting from (S)-N-benzylprolinehydrazide (1) is described. The reactions of 1b with isothiocyanates in refluxing MeOH led to the thiosemicarbazide 3 with a N-benzylprolinoyl residue. Thiosemicarbazide 3 underwent cyclization reactions under basic (NaOH) and acidic (H2SO4) conditions to yield (S)-prolinyl-substituted 1,2,4-triazole-3-thione 4 and 1,3,4-thiadiazole-2-amine 5, respectively.

GRAPHICAL ABSTRACT

Acknowledgments

The presented results summarize our recent efforts in the synthesis of enantiomerically pure bis-heterocycles containing (S)-proline moiety. Adam M. Pieczonka thanks for financial support within the project co-funded by the European Union under the European Social Fund “HUMAN – BEST INVESTMENT!.”

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