Download PDF
Synthesis 1996; 1996(1): 133-140
DOI: 10.1055/s-1996-4160
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Reactions of N-Unsubstituted 4-Amino-1-azadienes Towards Electrophiles

José Barluenga* , Carlos del Pozo, Bernardo Olano
  • *Instituto de Química Organometálica ”Enrique Moles”, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería 8, E-33071 Oviedo, Spain
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Several reactions related to the ambident nucleophilicity of N-unsubstituted azadienes 1 are described. Thus, reaction of 1 with alkylating agents and iodobispyridinium tetrafluoroborate (IPy2BF4) leads to the C-substituted azadienes 3 and 5 respectively. Azadienes 1 and 3 are converted to the carbonyl derivatives 2 and 4 by mild hydrolysis. On the other hand, azadienes 1, 3 and 5 react through the nitrogen atoms with several carbonyl centered electrophiles to give nitrogen heterocycles such as pyrimidines 6 and 9 and dihydropyrimidines 11. All those processes are totally regioselective, azadienes 1 and 3 showing a lower nucleophilicity at nitrogen than N-substituted azadienes.

N-unsubstituted 4-amino-1-azadienes - C-alkylation - pyrimidines - 2,3-dihydropyrimidines