Publication: New Optically Active Bis-Heterocycles Derived from (S)-Proline
New Optically Active Bis-Heterocycles Derived from (S)-Proline
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Pieczonka, A. M., Mlostoń, G., Linden, A., & Heimgartner, H. (2012). New Optically Active Bis-Heterocycles Derived from (S)-Proline. Helvetica Chimica Acta, 95(9), 1521–1530. https://doi.org/10.1002/hlca.201200400
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Enantiomerically pure bis-heterocycles containing a (S)-proline moiety have been prepared starting from (S)-N-benzylprolinehydrazide (2b). The reactions with isothiocyanates or butyl isocyanate in refluxing MeOH led to the corresponding thiosemicarbazide 5 and semicarbazide 9 with a N-benzylprolinoyl residue. The structure of the tert-butyl derivative 5d was established by X-ray crystallography. Base-catalyzed cyclization of 5 and 9 led to (S)-3-(pyrrolidin-2-yl)-1H-1,2,4-triazole-5(4H)-thiones 6 and the corresponding 5(4H)-one 8, res
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- Pieczonka, Adam M
- Mlostoń, Grzegorz
- Heimgartner, Heinz
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Pieczonka, A. M., Mlostoń, G., Linden, A., & Heimgartner, H. (2012). New Optically Active Bis-Heterocycles Derived from (S)-Proline. Helvetica Chimica Acta, 95(9), 1521–1530. https://doi.org/10.1002/hlca.201200400
