The iron-catalyzed construction of 2-aminopyrimidines from alkynenitriles and cyanamides

Several cycloaddition catalysts and reagents were surveyed for their effectiveness toward cyclizing alkynenitriles with cyanamides. Catalytic amounts of FeI2, (iPr)PDAI and Zn were found to effectively catalyze the [2+2+2] cycloaddition of a variety of cyanamides and alkynenitriles to afford bicycli...

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Published inChemical communications (Cambridge, England) Vol. 49; no. 70; pp. 7735 - 7737
Main Authors Lane, Timothy K., Nguyen, Minh H., D'Souza, Brendan R., Spahn, Nathan A., Louie, Janis
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 11.09.2013
Subjects
Alkynes
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ALPHA,OMEGA-DIYNES
COMPLEXES
ISOCYANATES
2+2+2 CYCLOADDITION
INHIBITORS
ALKYNES
CYCLOTRIMERIZATION
DERIVATIVES
SUBSTITUTED PYRIDINES
DIYNES
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Summary:Several cycloaddition catalysts and reagents were surveyed for their effectiveness toward cyclizing alkynenitriles with cyanamides. Catalytic amounts of FeI2, (iPr)PDAI and Zn were found to effectively catalyze the [2+2+2] cycloaddition of a variety of cyanamides and alkynenitriles to afford bicyclic 2-aminopyrimidines.
Bibliography:Medline
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ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc44422h