Journal
TETRAHEDRON LETTERS
Volume 52, Issue 16, Pages 1895-1897Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.02.042
Keywords
Polyamines; Cyclic amidines; N-Acylation; Cyclodehydration; Microwaves
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Funding
- University of Buenos Aires
- CONICET
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In the present Letter we report the use of N-arylputrescines as synthetic intermediates for the preparation of N-acyl-N'-aryltetramethylenediamines 3 and related seven-membered heterocyclic amidines 4. Compounds 1 were synthesized by Cs2CO3/KI-mediated aminolysis of 4-chlorobutyronitrile and subsequent reduction. N-Acylation of diamines 1 with carboxylic acid anhydrides led selectively to N-acyl-N'-aryl tetramethylenediamines 3. Microwave-assisted ring closure of such precursors promoted by PPE allowed for the synthesis of hitherto unreported 1-aryl-2-alkyl-1H-1,4,5,6-tetrahydro-1,3-diazepines 4. (C) 2011 Elsevier Ltd. All rights reserved.
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