A Novel Approach to the Synthesis of Medium Ring Nitrogen Heterocycles
- 1 January 1990
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1990 (10) , 584-586
- https://doi.org/10.1055/s-1990-21173
Abstract
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.Keywords
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