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Updated: May 10, 2026

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Cyclodehydration of N-(aminoalkyl)benzamides under mild conditions with a Hendrickson reagent analogue
Wendy A Loughlin1, Ian D Jenkins, Maria J Petersson
1School of Biomolecular and Physical Sciences, Griffith University, Nathan, QLD 4111, Australia.
Abstract:
Methods for the cyclodehydration of N-(aminoalkyl)benzamides are few and employ harsh reaction conditions. We have found that the easily prepared phosphonium anhydrides 1 (Hendrickson reagent) or 2 can be used for cyclodehydration of N-(aminoalkyl)benzamides under very mild conditions (room temperature) to produce five-, six-, and seven-membered cyclic amidines. Good yields are obtained by employing a temporary trityl group protection strategy. Cyclic analogue 2 can be used when the product cyclic amidine is organic-soluble, thus producing water-soluble byproducts.
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