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A Method to Access Symmetrical Tetrasubstituted Pyridines via Iodine and Ammonium Persulfate Mediated [2+2+1+1]‐Cycloaddition Reaction
Author(s) -
Liu Weibing,
Tan Hua,
Chen Cui,
Pan Yupeng
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601225
Subject(s) - chemistry , cycloaddition , ammonium persulfate , formamide , iodine , substrate (aquarium) , medicinal chemistry , pyridine , pyrimidine , catalysis , combinatorial chemistry , organic chemistry , stereochemistry , polymerization , oceanography , geology , polymer
A novel metal‐free [2+2+1+1]‐cycloaddition method for rapid and productive preparation of symmetrical 2,3,5,6‐tetrasubstituted pyridines has been developed from α‐substituted arones and N,N‐dimethyl formamide (DMF) using iodine (I 2 ) and ammonium persulfate ((NH 4 ) 2 S 2 O 8 ) as mediators. In this process, both DMF and (NH 4 ) 2 S 2 O 8 play a dual role for the formation of pyridines. DMF acts as the reaction medium and the C4 source (the methyl group of DMF), while (NH 4 ) 2 S 2 O 8 serves as the oxidant and nitrogen resource. Notably, this transformation exhibited a broad substrate scope towards a wide variety of different arones to give the corresponding tetrasubstituted pyridines in moderate to excellent yields.