Diethoxyphosphoryl as a protecting-activating group in the synthesis of polyazacyclophanes

Andrea Chellini; Roberto Pagliarin; Giovanni B. Giovenzanna; Giovanni Palmisano; Massimo Sisti

doi: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

Andrea Chellini
, Roberto Pagliarin
, Giovanni B. Giovenzanna
, Giovanni Palmisano
, Massimo Sisti

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	793-800
Number of pages	8
Journal	Helvetica Chimica Acta
Volume	83
Issue number	4
DOIs	https://doi.org/10.1002/(SICI)1522-2675(20000412)83:4<793::AID-HLCA793>3.0.CO;2-3
Publication status	Published - 2000
Externally published	Yes

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10.1002/(SICI)1522-2675(20000412)83:4<793::AID-HLCA793>3.0.CO;2-3

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title = "Diethoxyphosphoryl as a protecting-activating group in the synthesis of polyazacyclophanes",

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.",

author = "Andrea Chellini and Roberto Pagliarin and Giovenzanna, \{Giovanni B.\} and Giovanni Palmisano and Massimo Sisti",

year = "2000",

doi = "10.1002/(SICI)1522-2675(20000412)83:4<793::AID-HLCA793>3.0.CO;2-3",

language = "English",

volume = "83",

pages = "793--800",

journal = "Helvetica Chimica Acta",

issn = "0018-019X",

publisher = "Wiley-Blackwell",

number = "4",

}

TY - JOUR

T1 - Diethoxyphosphoryl as a protecting-activating group in the synthesis of polyazacyclophanes

AU - Chellini, Andrea

AU - Pagliarin, Roberto

AU - Giovenzanna, Giovanni B.

AU - Palmisano, Giovanni

AU - Sisti, Massimo

PY - 2000

Y1 - 2000

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0034016809

U2 - 10.1002/(SICI)1522-2675(20000412)83:4<793::AID-HLCA793>3.0.CO;2-3

DO - 10.1002/(SICI)1522-2675(20000412)83:4<793::AID-HLCA793>3.0.CO;2-3

M3 - Article

SN - 0018-019X

VL - 83

SP - 793

EP - 800

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 4

ER -

Diethoxyphosphoryl as a protecting-activating group in the synthesis of polyazacyclophanes

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