Aqueous N-Heterocyclization of Primary Amines and Hydrazines with Dihalides:  Microwave-Assisted Syntheses of N-Azacycloalkanes, Isoindole, Pyrazole, Pyrazolidine, and Phthalazine Derivatives

Yuhong Ju and Rajender S. Varma*;
Clean Processes Branch, Sustainable Technology Division, National Risk Management Research Laboratory, U.S. Environmental Protection Agency, 26 West Martin Luther King Drive, MS 443, Cincinnati, Ohio 45268
J. Org. Chem., 2006, 71 (1), pp 135–141
DOI: 10.1021/jo051878h
Publication Date (Web): November 30, 2005
Copyright © 2006 American Chemical Society
*

 To whom correspondence should be addressed. Phone:  +1-513-487-2701. Fax:  +1-513-569-7677.

, Ju.Yuhong@epa.gov, ; , Varma.Rajender@epa.gov

Abstract

Abstract Image

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.

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History

  • Published In Issue January 06, 2006
  • Received September 7, 2005

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