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Malononitrile as a carbonyl synthon: a one-pot preparation of heteroaryl amide via a SNAr-oxidation–displacement strategy
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Jul2004, Vol. 45 Issue 30, p5909-5911. 3p. - Publication Year :
- 2004
-
Abstract
- Malononitrile could be utilized as a synthon for the carbonyl moiety via a one-pot process that was initiated via base-mediated SNAr substitution of a heteroaryl halide. Subsequent peracetic acid oxidation of the resultant anion delivered an electrophilic acyl nitrile in situ that readily reacted with added nucleophiles to afford heteroaryl carboxylic acid derivatives. The reaction of the sodium salt of malononitrile with a series of heteroaryl chlorides followed by the subsequent addition of an amine and peracetic acid provided the corresponding heteroaryl amides. [Copyright &y& Elsevier]
- Subjects :
- *AMIDES
*CONDENSATION
*OXIDATION
*NUCLEOPHILIC reactions
Subjects
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 45
- Issue :
- 30
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 13622969
- Full Text :
- https://doi.org/10.1016/j.tetlet.2004.05.154