Aqueous N-heterocyclization of primary amines and hydrazines with dihalides: microwave-assisted syntheses of N-azacycloalkanes, isoindole, pyrazole, pyrazolidine, and phthalazine derivatives

J Org Chem. 2006 Jan 6;71(1):135-41. doi: 10.1021/jo051878h.

Abstract

[reactions: see text] The synthesis of nitrogen-containing heterocycles from alkyl dihalides (ditosylates) and primary amines and hydrazines via a simple and efficient cyclocondensation in an alkaline aqueous medium that occurs under microwave irradiation is described. This improved greener synthetic methodology provides a simple and straightforward one-pot approach to the synthesis of a variety of heterocycles, such as substituted azetidines, pyrrolidines, piperidines, azepanes, N-substituted 2,3-dihydro-1H-isoindoles, 4,5-dihydropyrazoles, pyrazolidines, and 1,2-dihydrophthalazines.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkanes / chemical synthesis
  • Alkanes / chemistry*
  • Alkylation
  • Amines / chemistry*
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Cyclization
  • Hot Temperature
  • Hydrazines / chemistry*
  • Hydrogen / chemistry
  • Indoles / chemistry*
  • Isomerism
  • Microwaves
  • Molecular Structure
  • Molecular Weight
  • Nitrogen / chemistry
  • Phthalazines / chemistry*
  • Pyrazoles / chemistry*

Substances

  • Alkanes
  • Amines
  • Aza Compounds
  • Hydrazines
  • Indoles
  • Phthalazines
  • Pyrazoles
  • pyrazole
  • Hydrogen
  • phthalazine
  • Nitrogen