Cyclodehydration of N-(Aminoalkyl)benzamides under Mild Conditions with a Hendrickson Reagent Analogue

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Loughlin, Wendy A
Jenkins, Ian D
Petersson, Maria J
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2013
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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 byproduc

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The Journal of Organic Chemistry

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78

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14

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Medicinal and biomolecular chemistry

Organic chemistry

Organic chemical synthesis

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