Direct, metal-free amination of heterocyclic amides/ureas with NH-heterocycles and N-substituted anilines in POCl3

J Org Chem. 2011 Oct 21;76(20):8262-9. doi: 10.1021/jo201425q. Epub 2011 Sep 7.

Abstract

A POCl(3)-mediated, direct amination reaction of heterocyclic amides/ureas with NH-heterocycles or N-substituted anilines is described. Compared to the existing methods, this operationally simple protocol provides unique reactivity and functional group compatibility because of the metal-free, acidic reaction conditions. The yields are generally excellent.

MeSH terms

  • Amides / chemistry*
  • Amination
  • Aniline Compounds / chemistry
  • Anticholesteremic Agents / analysis
  • Anticholesteremic Agents / chemistry
  • Azabicyclo Compounds / analysis
  • Azabicyclo Compounds / chemistry
  • Benzamides
  • Catalysis
  • Chemistry, Pharmaceutical / methods*
  • Erlotinib Hydrochloride
  • Eszopiclone
  • Fluorobenzenes / analysis
  • Fluorobenzenes / chemistry
  • Heterocyclic Compounds / analysis
  • Heterocyclic Compounds / chemical synthesis*
  • Humans
  • Hydrogen-Ion Concentration
  • Hypnotics and Sedatives / analysis
  • Hypnotics and Sedatives / chemistry
  • Hypoglycemic Agents / analysis
  • Hypoglycemic Agents / chemistry
  • Imatinib Mesylate
  • Molecular Structure
  • Phosphorus Compounds / chemistry
  • Piperazines / analysis
  • Piperazines / chemistry
  • Prescription Drugs / analysis
  • Prescription Drugs / chemical synthesis*
  • Protein Kinase Inhibitors / analysis
  • Protein Kinase Inhibitors / chemistry
  • Pyrimidines / analysis
  • Pyrimidines / chemistry
  • Quinazolines / analysis
  • Quinazolines / chemistry
  • Rosiglitazone
  • Rosuvastatin Calcium
  • Sulfonamides / analysis
  • Sulfonamides / chemistry
  • Thiazolidinediones / analysis
  • Thiazolidinediones / chemistry
  • Urea / analogs & derivatives
  • Urea / chemistry*

Substances

  • Amides
  • Aniline Compounds
  • Anticholesteremic Agents
  • Azabicyclo Compounds
  • Benzamides
  • Fluorobenzenes
  • Heterocyclic Compounds
  • Hypnotics and Sedatives
  • Hypoglycemic Agents
  • Phosphorus Compounds
  • Piperazines
  • Prescription Drugs
  • Protein Kinase Inhibitors
  • Pyrimidines
  • Quinazolines
  • Sulfonamides
  • Thiazolidinediones
  • Rosiglitazone
  • Rosuvastatin Calcium
  • Imatinib Mesylate
  • Urea
  • phosphoryl chloride
  • Erlotinib Hydrochloride
  • aniline
  • Eszopiclone