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Synthesis 2013; 45(1): 93-100
DOI: 10.1055/s-0032-1316819
DOI: 10.1055/s-0032-1316819
paper
Structural Reorganization of Allyl Isothiocyanate into Pyrrole Ring under Superbase: A Straightforward Access to NH-2-(Alkylsulfanyl)-1H-pyrroles and N-Alkyl-2-(alkylsulfanyl)-1H-pyrroles
Further Information
Publication History
Received: 02 September 2012
Accepted after revision: 07 November 2012
Publication Date:
26 November 2012 (online)
Abstract
A novel and facile synthetic route to NH-2-(alkylsulfanyl)-1H-pyrroles and N-alkyl-2-(alkylsulfanyl)-1H-pyrroles is reported. This was achieved by deprotonation of allyl isothiocyanate with the superbasic pair lithium diisopropylamide and potassium tert-butoxide (1:1 molar mixture), followed by intramolecular ring closure, deprotonation of cyclic anion with a second equivalent of the superbase, and final sequential N-protolysis/S-alkylation or N,S-dialkylation of the formed N,S-centered pyrrol-2-ylsulfide dianion.
Key words
2-(alkylsulfanyl)-substituted pyrroles - allyl isothiocyanate - superbases - deprotonation - cyclization - alkylationSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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