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Azodicarboxamides vs. Azodicarboxylates in Reactions against Thioisomünchnones: 1,3‐Dipolar Cycloaddition or Nucleophilic Addition?
Author(s) -
Sánchez Bárbara,
López Ignacio,
Light Mark E.,
Silvero Guadalupe,
Bravo José Luis
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901349
Subject(s) - chemistry , mesoionic , cycloaddition , nucleophile , fragmentation (computing) , 1,3 dipolar cycloaddition , toluene , computational chemistry , yield (engineering) , nucleophilic addition , dipole , photochemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , computer science , metallurgy , operating system
This communication presents the first study on the use of azodicarboxamides against mesoionic heterocycles as 1,3‐dipoles. The reactions yield thioureido compounds. Their formation could be explained, on the basis of experimental results and preliminary theoretical calculations, by a nucleophilic addition followed by rearrangement; however, a formal 1,3‐dipolar cycloaddition and subsequent fragmentation and rearrangement of the transient cycloadducts could not be ruled out. Reactions are carried out in refluxing toluene and are complete in 90–240 min. Structural elucidation of the products is based on single‐crystal X‐ray analysis, as well as other spectroscopic data and 2D‐NMR correlations.