Amination of heterocyclic compounds with o-benzoylhydroxylamine derivatives.
The N-amination of heterocyclic compounds 1a-k with O-benzoylhydroxylamine derivatives 5 was developed and demonstrated to be a superior alternative to existing N-amination methods. A structure-reactivity relationship study was performed on variously substituted O-benzoylhydroxylamine derivatives, leading to the discovery of the novel and more efficient aminating reagents 5h and 5i.
Parlanti
Luca
L
Department of Process Research and Development and Drug Discovery Chemistry, Bristol-Myers Squibb Research & Development, PO Box 4000, Princeton, New Jersey 08543, USA.
Discordia
Robert P
RP
Hynes
John
J
Miller
Michael M
MM
O'Grady
Harold R
HR
Shi
Zhongping
Z
D000586:Amination; D000838:Anions; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D006898:Hydroxylamines / Q000737:chemistry*; D007536:Isomerism; D007700:Kinetics; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry; D014227:Triazines / Q000737:chemistry; D014867:Water / Q000737:chemistry
D000838:Anions; D006571:Heterocyclic Compounds; D006898:Hydroxylamines; D011758:Pyrroles; D014227:Triazines; D014867:Water; C010046:O-benzoylhydroxylamine