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On the synthesis of the first representatives of bis(benzo)bispidinoaza-14-crown-4 ethers



Chemistry of Heterocyclic Compounds, Vol. 44, No. 5, 2008 A. I. Komarova1, A. N. Levov2, A. T. Soldatenkov2, and S. A. Soldatova2 Keywords: bis(benzo)bispidinoaza-14-crown-4-ethers, condensation with aromatic aldehydes and ammonia. In previous work [1-3], we reported the first syntheses of dibenzoazacrown ethers containing a constituent γ-piperidone fragment in the macrocycle. This success led us to consider the possibility of using these compounds for the construction of a new, more complicated heterocyclic system containing a bispidine fragment in the crown ether part of the macrocycle. Hence, we studied the condensation of azacrownophane 1 [3] with aromatic aldehydes 2a,b and ammonium acetate. Maintenance of this mixture in a solution of ethanol and acetic acid for seven days at 20°C followed by crystallization gave compounds 3a in 15% yield and 3b in 11% yield. These azacrown ethers belong to a new group of lariat ethers [4], in which the constituent H N 24 O N H O O 1 O + RCHO + NH4OAc 2a,b N H 7 O 10 O 15 16 O 13 2, 3 a R = 4-FC6H4, b R = (MeO)2C6H3 3a,b 3,7-diazabicyclo[3.3.1]nonane fragment has additional sites for coordination with metal cations. These sites are auxiliary upon



Chemistry of Heterocyclic CompoundsSpringer Journals

Published: May 1, 2008

DOI: 10.1007/s10593-008-0084-7

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