Expeditious N-Monoalkylation of 1,4,7,10-Tetraazacyclododecane (Cyclen) via Formamido Protection

V. BOLDRINI; Giovanni Battista GIOVENZANA; R. PAGLIARIN; G. PALMISANO; M. SISTI

doi:10.1016/S0040-4039(00)01092-3

Expeditious N-Monoalkylation of 1,4,7,10-Tetraazacyclododecane (Cyclen) via Formamido Protection

V. BOLDRINI, Giovanni Battista GIOVENZANA, R. PAGLIARIN, G. PALMISANO, M. SISTI

Department of Pharmaceutical Sciences

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

Abstract

The reaction of cyclen 1 with chloral hydrate afforded exclusively 1,4,7-triformylcyclen 2 in high yield; the triprotected macrocycle was easily alkylated with various electrophiles in good to excellent yields. The alkaline removal of the formyl groups provided a selective entry into N-monosubstituted cyclen derivatives.

Original language	English
Pages (from-to)	6527-6530
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4039(00)01092-3
Publication status	Published - 2000

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10.1016/S0040-4039(00)01092-3

http://hdl.handle.net/11579/9652

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@article{b20f1c7376844f09980300e8be3725fc,

title = "Expeditious N-Monoalkylation of 1,4,7,10-Tetraazacyclododecane (Cyclen) via Formamido Protection",

abstract = "The reaction of cyclen 1 with chloral hydrate afforded exclusively 1,4,7-triformylcyclen 2 in high yield; the triprotected macrocycle was easily alkylated with various electrophiles in good to excellent yields. The alkaline removal of the formyl groups provided a selective entry into N-monosubstituted cyclen derivatives.",

author = "V. BOLDRINI and GIOVENZANA, \{Giovanni Battista\} and R. PAGLIARIN and G. PALMISANO and M. SISTI",

note = "Funding Information: This work was supported by CNR, Rome, through Target project on {\textquoteleft}Biotechnology{\textquoteright}. Professor S. Aime (University of Turin) is gratefully acknowledged for his interest and helpful discussions. ",

year = "2000",

doi = "10.1016/S0040-4039(00)01092-3",

language = "English",

volume = "41",

pages = "6527--6530",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - Expeditious N-Monoalkylation of 1,4,7,10-Tetraazacyclododecane (Cyclen) via Formamido Protection

AU - BOLDRINI, V.

AU - GIOVENZANA, Giovanni Battista

AU - PAGLIARIN, R.

AU - PALMISANO, G.

AU - SISTI, M.

N1 - Funding Information: This work was supported by CNR, Rome, through Target project on ‘Biotechnology’. Professor S. Aime (University of Turin) is gratefully acknowledged for his interest and helpful discussions.

PY - 2000

Y1 - 2000

N2 - The reaction of cyclen 1 with chloral hydrate afforded exclusively 1,4,7-triformylcyclen 2 in high yield; the triprotected macrocycle was easily alkylated with various electrophiles in good to excellent yields. The alkaline removal of the formyl groups provided a selective entry into N-monosubstituted cyclen derivatives.

AB - The reaction of cyclen 1 with chloral hydrate afforded exclusively 1,4,7-triformylcyclen 2 in high yield; the triprotected macrocycle was easily alkylated with various electrophiles in good to excellent yields. The alkaline removal of the formyl groups provided a selective entry into N-monosubstituted cyclen derivatives.

UR - https://iris.uniupo.it/handle/11579/9652

U2 - 10.1016/S0040-4039(00)01092-3

DO - 10.1016/S0040-4039(00)01092-3

M3 - Article

SN - 0040-4039

VL - 41

SP - 6527

EP - 6530

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

Expeditious N-Monoalkylation of 1,4,7,10-Tetraazacyclododecane (Cyclen) via Formamido Protection

Abstract

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