Download PDF
Synlett 1990; 1990(10): 584-586
DOI: 10.1055/s-1990-21173
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A Novel Approach to the Synthesis of Medium Ring Nitrogen Heterocycles

Robert Shaw* , Martin Anderson, Timothy Gallagher
  • *Shell Research Limited, Sittingbourne Research Centre, Sittingbourne, Kent ME9 8AG, England and School of Chemistry, Bath University, Bath BA2 7AY, England
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Addition of iodine to the N-sulphonyl allenic amines 4 [ω-(4-toluenesulphonamido)-1,2-alkadienes] gives allylic iodides 5 [1,2-diiodo-ω-(4-toluenesulphonamido)-2-alkenes] which undergo cyclisation on treatment with sodium hydride. For 5a (n= 1) the "exo" cyclisation product 6 predominated but for 5b-e (n= 2-5) cyclisation to give the "endo" product 7, the larger of the two possible ring sizes, was the major pathway observed. In this way 8-11 membered azamacrocycles have been prepared in 35-62% yield.

      >