Journal of Heterocyclic Chemistry p. 1431 - 1438 (2000)
Update date:2022-08-03
Topics:
Hedrera
Perillo
The synthesis of several 1,2-diaryl-1H-4,5,6,7-tetrahydro-1,3-diazepines 1 by cyclization of N-aryl-N′-benzoyltetramethylenediamines 2 is described. Two alternative synthetic routes to obtain precursors 2 are discussed, being that which employes pyrrolidine as starting material the most convenient. Nucleophilic attack of compounds 1 on methyl iodide affords 1,2-diaryl-1H-4,5,6,7-tetrahydro-1,3-diazepinium iodides 3. 1H-nmr spectra of these compounds are unequivocally assigned by means of NOESY experiments. 1H-nmr spectra of compounds 1 and 3 are analyzed and compared inter se and with those of compounds 1 run in the presence of trifluoroacetic acid-d. Reduction of compounds 1 with borane leads regiospecifically to N-aralkyl-N′-aryltetramethylenediamines 7.
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