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Synlett 2001; 2001(1): 0057-0060
DOI: 10.1055/s-2001-9710
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Aminopyrimidines as Electron-Rich Azadienes: Extension of the Synthetic Potential of Hetero Diels-Alder Reactions under Acidic Conditions

Celeste García* , Manuel Melguizo, Justo Cobo, Adolfo Sánchez, Manuel Nogueras, M. Dolores López
  • *Departamento de Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071-Jaén, Spain; Fax 34-9 53 01 21 51; E-mail: mmelgui@ujaen.es
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Publication Date:
31 December 2001 (online)

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By addition of a catalytic amount of a strong acid and selection of the appropriate solvent, the cycloaddition reactions of dimethyl acetylenedicarboxylate (DMAD) to 6-aminopyrimidine derivatives drastically changed their course leading to new products, pyrrolo[3,4-c]pyridines, which were different from those obtained in the absence of acid. This change was interpreted on the basis of acid interception of the non-isolable adducts formed by initial hetero Diels-Alder cycloaddition between the reactants.

hetero Diels-Alder reactions - glycosides - heterocycles - pyrimidines - tandem reactions

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