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Preparation of macrocyclic di‐ and tetraamides containing unsubstituted macroring nitrogen atoms, tertiary amine sidearms and/or piperazine subcyclic units
Author(s) -
Bradshaw Jerald S.,
Krakowiak Krzysztof E.,
An Haoyun,
Izatt Reed M.
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270748
Subject(s) - chemistry , piperazine , tertiary amine , amine gas treating , cyclophane , borane , crown (dentistry) , medicinal chemistry , organic chemistry , stereochemistry , crystal structure , medicine , dentistry , catalysis
Seven new macrocyclic di‐ and tetramides have been prepared by the cyclization reaction of various polyamines or, in one case, a dimercaptan with a bis(α‐chloroamide) or diethyl malonate. Three of the resulting macrocyclic diamides were reduced with borane to form the corresponding polyaza‐crown analogs. Macrocycles prepared include two tetraaza‐12‐crown‐4, two tetraaza‐13‐crown‐4, two tetraaza‐14‐crown‐4, one dithiadiaza‐14‐crown‐4, one tetraaza‐15‐crown‐4 with a piperazine subcyclic group, one dibenzotetraaza‐24‐crown‐8 and one octaaza‐30‐crown‐8 with two piperazine subcyclic groups.