{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Bachollet SP"],"funding":["Engineering and Physical Sciences Research Council"],"pagination":["12889-93"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC4313684"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["20(40)"],"pubmed_abstract":["The aza-Diels-Alder cycloaddition of 1,2,4-triazines with alkynes offers a rapid and convenient method for the synthesis of highly substituted pyridines, but often requires harsh conditions and long reaction times. The present study offers a solution to these limitations by use of a temporary tether established by a Lewis acid-base complexation of in situ generated alkynylboranes and triazines bearing a Lewis basic donor. The cycloaddition reactions take place within 20 min at 40 °C and provide direct access to a broad range of pyridines with complete and predictable regiocontrol. The carbonboron bond can be further functionalised by cross-coupling allowing further functionality to be introduced after cycloaddition."],"journal":["Chemistry (Weinheim an der Bergstrasse, Germany)"],"pubmed_title":["Development of a mild and versatile directed cycloaddition approach to pyridines."],"pmcid":["PMC4313684"],"funding_grant_id":["EP/D03213X/1"],"pubmed_authors":["Cocker DC","Bachollet SP","Harrity JP","Vivat JF","Adams H"],"additional_accession":[]},"is_claimable":false,"name":"Development of a mild and versatile directed cycloaddition approach to pyridines.","description":"The aza-Diels-Alder cycloaddition of 1,2,4-triazines with alkynes offers a rapid and convenient method for the synthesis of highly substituted pyridines, but often requires harsh conditions and long reaction times. The present study offers a solution to these limitations by use of a temporary tether established by a Lewis acid-base complexation of in situ generated alkynylboranes and triazines bearing a Lewis basic donor. The cycloaddition reactions take place within 20 min at 40 °C and provide direct access to a broad range of pyridines with complete and predictable regiocontrol. The carbonboron bond can be further functionalised by cross-coupling allowing further functionality to be introduced after cycloaddition.","dates":{"release":"2014-01-01T00:00:00Z","publication":"2014 Sep","modification":"2026-05-29T20:24:34.35Z","creation":"2019-03-27T01:44:25Z"},"accession":"S-EPMC4313684","cross_references":{"pubmed":["25145488"],"doi":["10.1002/chem.201403916"]}}