The fully diethoxyphosphoryl(Dep)-protected polyamines 1b-3b were prepared from the corresponding polyamines with 'diethyl phosphite' (= diethyl phosphonate) and CCl4 in a solid base/organic liquid two-phase system in the presence of Bu4NBr as phase-transfer catalyst. Subsequent phase-transfer-catalyzed alkylation of phosphoramidates 1b-3b with bis(chloromethyl)arenes 5-8 in the presence of Bu4N(HSO4) followed by deprotection gave good yields of polyazacyclophanes 9a-16a.
Diethoxyphosphoryl as a protecting-activating group in the synthesis of polyazacyclophanes / A. Chellini, R. Pagliarin, G. Giovenzana, G. Palmisano, M. Sisti. - In: HELVETICA CHIMICA ACTA. - ISSN 0018-019X. - 83:4(2000), pp. 793-800. [10.1002/(SICI)1522-2675(20000412)83:4<793::AID-HLCA793>3.0.CO;2-3]
Diethoxyphosphoryl as a protecting-activating group in the synthesis of polyazacyclophanes
R. PagliarinSecondo
;
2000
Abstract
The fully diethoxyphosphoryl(Dep)-protected polyamines 1b-3b were prepared from the corresponding polyamines with 'diethyl phosphite' (= diethyl phosphonate) and CCl4 in a solid base/organic liquid two-phase system in the presence of Bu4NBr as phase-transfer catalyst. Subsequent phase-transfer-catalyzed alkylation of phosphoramidates 1b-3b with bis(chloromethyl)arenes 5-8 in the presence of Bu4N(HSO4) followed by deprotection gave good yields of polyazacyclophanes 9a-16a.
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