Synthesis and characterization of various unsubstituted and mono-N-substituted tetraazamacrocycles
作者:
I. Meunier,
A.K. Mishra,
B. Hanquet,
R. Guilard,
P. Cocolios,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1995)
卷期:
Volume 73,
issue 5
页码: 685-695
ISSN:0008-4042
年代: 1995
DOI:10.1139/v95-087
出版商: NRC Research Press
数据来源: NRC
摘要:
Syntheses of tetraazamacrocycles have been carried out by usingp-toluenesulfonyl chloride as protective group. The [14(ane) N4] and [15(ane) N4] were also obtained by the template synthesis. Mono-N-functionalization of tetraazamacrocycles was accomplished by reaction of a fivefold excess of the free macrocycles with 1 equivalent of a suitable alkylating or arylating reagent. The key point of the synthesis lies in the use of an excess of the macrocycle over the substituting reactants to reduce the formation of polysubstituted derivatives, and in the easy separation of the excess of unreacted macrocycle. All the products were characterized on the basis of spectral studies (1H andl3C NMR, including 2D NMR and NOE difference studies) and mass spectrometry.Keywords: tetraazamacrocycles, improved synthesis, protective group, N-tosylation, template synthesis, NOE difference spectroscopy.
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