Remote protection prevents unwanted cyclizations with 2-aminopyridines

Graham R. Lawton; Haitao Ji; Richard B. Silverman

doi:10.1016/j.tetlet.2006.06.091

Remote protection prevents unwanted cyclizations with 2-aminopyridines

Graham R. Lawton, Haitao Ji, Richard B. Silverman^*

^*Corresponding author for this work

Chemistry

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

13 Scopus citations

Abstract

The pyridine nitrogen of the 2-aminopyridine group is sufficiently nucleophilic to undergo intramolecular cyclizations, thereby preventing competing Mitsunobu and other substitution reactions from proceeding at a remote site. Double protection of the 2-amino group effectively blocked reaction at the pyridine nitrogen. This is a rare example of the use of a remote protecting group to block another group from reacting.

Original language	English (US)
Pages (from-to)	6113-6115
Number of pages	3
Journal	Tetrahedron Letters
Volume	47
Issue number	34
DOIs	https://doi.org/10.1016/j.tetlet.2006.06.091
State	Published - Aug 21 2006

Keywords

2-Aminopyridines
Mitsunobu reaction
Prevent cyclization
Remote protection
Side reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.06.091

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title = "Remote protection prevents unwanted cyclizations with 2-aminopyridines",

abstract = "The pyridine nitrogen of the 2-aminopyridine group is sufficiently nucleophilic to undergo intramolecular cyclizations, thereby preventing competing Mitsunobu and other substitution reactions from proceeding at a remote site. Double protection of the 2-amino group effectively blocked reaction at the pyridine nitrogen. This is a rare example of the use of a remote protecting group to block another group from reacting.",

keywords = "2-Aminopyridines, Mitsunobu reaction, Prevent cyclization, Remote protection, Side reaction",

author = "Lawton, {Graham R.} and Haitao Ji and Silverman, {Richard B.}",

note = "Funding Information: The authors are grateful to the National Institutes of Health (GM 49725) for financial support of this research. ",

year = "2006",

month = aug,

day = "21",

doi = "10.1016/j.tetlet.2006.06.091",

language = "English (US)",

volume = "47",

pages = "6113--6115",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - Remote protection prevents unwanted cyclizations with 2-aminopyridines

AU - Lawton, Graham R.

AU - Ji, Haitao

AU - Silverman, Richard B.

N1 - Funding Information: The authors are grateful to the National Institutes of Health (GM 49725) for financial support of this research.

PY - 2006/8/21

Y1 - 2006/8/21

N2 - The pyridine nitrogen of the 2-aminopyridine group is sufficiently nucleophilic to undergo intramolecular cyclizations, thereby preventing competing Mitsunobu and other substitution reactions from proceeding at a remote site. Double protection of the 2-amino group effectively blocked reaction at the pyridine nitrogen. This is a rare example of the use of a remote protecting group to block another group from reacting.

AB - The pyridine nitrogen of the 2-aminopyridine group is sufficiently nucleophilic to undergo intramolecular cyclizations, thereby preventing competing Mitsunobu and other substitution reactions from proceeding at a remote site. Double protection of the 2-amino group effectively blocked reaction at the pyridine nitrogen. This is a rare example of the use of a remote protecting group to block another group from reacting.

KW - 2-Aminopyridines

KW - Mitsunobu reaction

KW - Prevent cyclization

KW - Remote protection

KW - Side reaction

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DO - 10.1016/j.tetlet.2006.06.091

M3 - Article

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SN - 0040-4039

VL - 47

SP - 6113

EP - 6115

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

Remote protection prevents unwanted cyclizations with 2-aminopyridines

Abstract

Keywords

ASJC Scopus subject areas

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