Isothiourea-Mediated One-Pot Synthesis of Functionalized Pyridines

Acids to bases: The synthesis of 2,4,6‐trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β‐unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/lactamization, thiophenol elimination, and N‐ to O‐sulfonyl migration, giving 2‐sulfonate‐substi...

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Bibliographic Details
Published in:	Angewandte Chemie International Edition Vol. 52; no. 44; pp. 11642 - 11646
Main Authors:	Stark, Daniel G., Morrill, Louis C., Yeh, Pei-Pei, Slawin, Alexandra M. Z., O'Riordan, Timothy J. C., Smith, Andrew D.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 25-10-2013 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Edition:	International ed. in English
Subjects:	Catalysis Communications Cyclization heterocycles isothiourea Lewis base Migration Molecular Structure organocatalysis Pyridines Pyridines - chemical synthesis Pyridines - chemistry Stereoisomerism Synthesis Thiophenol Thiourea - chemistry organocatalysis Lewis base heterocycles cyclization isothiourea
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Summary:	Acids to bases: The synthesis of 2,4,6‐trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β‐unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/lactamization, thiophenol elimination, and N‐ to O‐sulfonyl migration, giving 2‐sulfonate‐substituted pyridines which are readily derivatized to generate structural diversity.
Bibliography:	ArticleID:ANIE201306786 Funded Access Carnegie Trust We thank the Royal Society (ADS), Syngenta/EPSRC (DGS), and The Carnegie Trust for the Universities of Scotland (LCM) for funding, and the EPSRC National Mass Spectrometry Service Centre (Swansea). The research leading to these results has received funding from the ERC under the European Union's 7th Framework Programme (FP7/2007-2013)/ERC grant agreement no. 279850. Syngenta EPSRC European Union - No. 279850 Royal Society ark:/67375/WNG-VJ5NGHWR-B istex:1F0D2C15EFC1318E3514075F69A4A93FFCB93F71 th We thank the Royal Society (ADS), Syngenta/EPSRC (DGS), and The Carnegie Trust for the Universities of Scotland (LCM) for funding, and the EPSRC National Mass Spectrometry Service Centre (Swansea). The research leading to these results has received funding from the ERC under the European Union’s 7 Framework Programme (FP7/2007‐2013)/ERC grant agreement no. 279850. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/anie.201306786.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201306786