Highly substituted 2-aminated indoles can be prepared in moderate to excellent yields by regioselective C2-amination of indoles promoted by iodine. As a key step in a concise synthesis of (±)-folicanthine, its core structure was easily obtained by one step cyclization-dimerization of substituted tryptophan in high yield on a gram scale.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/c2cc16637b | DOI Listing |
Org Biomol Chem
June 2024
Drugs for Neglected Diseases initiative, Chemin Camille-Vidart 15, 1202 Geneva, Switzerland.
The synthesis of a biologically relevant 2-amino-3-alkylamido 4-quinazolinone has been accomplished in four steps from commercially available materials using design principles from both modular and divergent synthesis. 3-Alkylation of 2-chloro-4(3)-quinazolinone using methyl bromoacetate, followed by C2-amination produced a suitable scaffold for introducing molecular diversity. Optimization of alkylation conditions afforded full regioselectivity, enabling exclusive access to the -alkylated isomer.
View Article and Find Full Text PDFOrg Biomol Chem
May 2013
Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA.
The C2 amination of imidazo[4,5-b]pyridines was accomplished through C2 halogenation followed by substitution (SNAr) with functionalized primary and secondary amines. This regioselective sequence is operationally simple and provides an easy access to derivatives of protected imidazo[4,5-b]pyridines.
View Article and Find Full Text PDFChem Commun (Camb)
February 2012
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
Highly substituted 2-aminated indoles can be prepared in moderate to excellent yields by regioselective C2-amination of indoles promoted by iodine. As a key step in a concise synthesis of (±)-folicanthine, its core structure was easily obtained by one step cyclization-dimerization of substituted tryptophan in high yield on a gram scale.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!