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Diethoxyphosphoryl as a Protecting‐Activating Group in the Synthesis of Polyazacyclophanes
Author(s) -
Chellini Andrea,
Pagliarin Roberto,
Giovenzana Giovanni B.,
Palmisano Giovanni,
Sisti Massimo
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(20000412)83:4<793::aid-hlca793>3.0.co;2-3
Subject(s) - chemistry , phosphonate , alkylation , catalysis , base (topology) , phase (matter) , organic chemistry , protecting group , phase transfer catalyst , group (periodic table) , medicinal chemistry , combinatorial chemistry , polymer chemistry , alkyl , mathematical analysis , mathematics
The fully diethoxyphosphoryl(Dep)‐protected polyamines 1b – 3b were prepared from the corresponding polyamines with `diethyl phosphite' (=diethyl phosphonate) and CCl 4 in a solid base/organic liquid two‐phase system in the presence of Bu 4 NBr as phase‐transfer catalyst. Subsequent phase‐transfer‐catalyzed alkylation of phosphoramidates 1b – 3b with bis(chloromethyl)arenes 5 – 8 in the presence of Bu 4 N(HSO 4 ) followed by deprotection gave good yields of polyazacyclophanes 9a – 16a .