Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 11, Pages 2152-2160Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101826
Keywords
Tetrazoles; 1,2-Diaza-1,3-butadienes; Nitrogen heterocycles; Aza-Diels-Alder reactions; Density functional calculations
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Funding
- Fundacao do Ministerio de Ciencia e Tecnologia (FCT) [SFRH/BD/45128/2008, PEst-C/QUI/UI0313/2011]
- Fundo Europeu de Desenvolvimento Regional (FEDER)
- Programa Operacional Factores de Competitividade (COMPETE)
- Quadro de Referencia Estrategico Nacional (QREN)
- Fundação para a Ciência e a Tecnologia [SFRH/BD/45128/2008] Funding Source: FCT
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The synthesis of new 3-tetrazolyl-1,4,5,6-tetrahydropyridazines by Diels-Alder reactions of ethyl 3-(tetrazol-5-yl)-1,2-diaza-1,3-butadiene-1-carboxylates is reported. These 1,2-diaza-1,3-dienes reacted with electron-rich heterocycles, nu-cleophilic olefins and cumulenes, as well as with electrondeficient dienophiles, to give the target compounds regioselectively. Computational studies corroborated the rationalization of the observed reactivity and selectivity.
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