Back to Search
Start Over
Simple Synthetic Approach to N -(Pyridin-2-yl)imidates from Nitrostyrenes and 2-Aminopyridines via the N -(Pyridin-2-yl)iminonitriles as Intermediates.
- Source :
-
Molecules . Apr2023, Vol. 28 Issue 8, p3321. 13p. - Publication Year :
- 2023
-
Abstract
- A facile, green, synthetic protocol of several substituted N-(pyridin-2-yl)imidates from nitrostyrenes and 2-aminopyridines via the corresponding N-(pyridin-2-yl)iminonitriles as intermediates is reported. The reaction process involved the in situ formation of the corresponding α-iminontriles under heterogeneous Lewis acid catalysis in the presence of Al2O3. Subsequently, α-iminonitriles were selectively transformed into the desired N-(pyridin-2-yl)imidates under ambient conditions and in the presence of Cs2CO3 in alcoholic media. Under these conditions, 1,2- and 1,3-propanediols also led to the corresponding mono-substituted imidates at room temperature. The present synthetic protocol was also developed on one mmol scale, providing access to this important scaffold. A preliminary synthetic application of the present N-(pyridin-2-yl)imidates was carried out for their facile conversion into the N-heterocycles 2-(4-chlorophenyl)-4,5-dihydro-1H-imidazole and 2-(4-chlorophenyl)-1,4,5,6-tetrahydropyrimidine in the presence of the corresponding ethylenediamine and 1,3-diaminopropane. [ABSTRACT FROM AUTHOR]
- Subjects :
- *LEWIS acids
*ETHYLENEDIAMINE
*AMINOPYRIDINES
*ALUMINUM oxide
*CATALYSIS
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 28
- Issue :
- 8
- Database :
- Academic Search Index
- Journal :
- Molecules
- Publication Type :
- Academic Journal
- Accession number :
- 163455578
- Full Text :
- https://doi.org/10.3390/molecules28083321