Effect of the leaving group on the reaction of 2-aminopyrroles with electron deficient heteroaromatic azadienes: substitution by addition-elimination versus cycloaddition

Michael De Rosa; David Arnold; Miroslav Medved'

doi:10.1016/j.tetlet.2007.04.036

Effect of the leaving group on the reaction of 2-aminopyrroles with electron deficient heteroaromatic azadienes: substitution by addition-elimination versus cycloaddition

Michael De Rosa, David Arnold, Miroslav Medved'

Penn State Brandywine

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

11 Scopus citations

Abstract

When a good leaving group is present in the heteroaromatic azadiene, reaction with 2-aminopyrroles occurs by substitution by addition-elimination instead of cycloaddition. This novel reaction is sensitive to steric effects and takes place in 2-amino-1-methylpyrrole at C-5 and the exo amino group but at C-3 in 2-amino-1-t-butylpyrrole.

Original language	English (US)
Pages (from-to)	3991-3994
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2007.04.036
State	Published - Jun 4 2007

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.04.036

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title = "Effect of the leaving group on the reaction of 2-aminopyrroles with electron deficient heteroaromatic azadienes: substitution by addition-elimination versus cycloaddition",

abstract = "When a good leaving group is present in the heteroaromatic azadiene, reaction with 2-aminopyrroles occurs by substitution by addition-elimination instead of cycloaddition. This novel reaction is sensitive to steric effects and takes place in 2-amino-1-methylpyrrole at C-5 and the exo amino group but at C-3 in 2-amino-1-t-butylpyrrole.",

author = "{De Rosa}, Michael and David Arnold and Miroslav Medved'",

note = "Funding Information: This work was supported by grant CHE-0110801 from the National Science Foundation. We thank Dr. J. Honovich (Drexel University) for mass spectra.",

year = "2007",

month = jun,

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doi = "10.1016/j.tetlet.2007.04.036",

language = "English (US)",

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pages = "3991--3994",

journal = "Tetrahedron Letters",

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T1 - Effect of the leaving group on the reaction of 2-aminopyrroles with electron deficient heteroaromatic azadienes

T2 - substitution by addition-elimination versus cycloaddition

AU - De Rosa, Michael

AU - Arnold, David

AU - Medved', Miroslav

N1 - Funding Information: This work was supported by grant CHE-0110801 from the National Science Foundation. We thank Dr. J. Honovich (Drexel University) for mass spectra.

PY - 2007/6/4

Y1 - 2007/6/4

N2 - When a good leaving group is present in the heteroaromatic azadiene, reaction with 2-aminopyrroles occurs by substitution by addition-elimination instead of cycloaddition. This novel reaction is sensitive to steric effects and takes place in 2-amino-1-methylpyrrole at C-5 and the exo amino group but at C-3 in 2-amino-1-t-butylpyrrole.

AB - When a good leaving group is present in the heteroaromatic azadiene, reaction with 2-aminopyrroles occurs by substitution by addition-elimination instead of cycloaddition. This novel reaction is sensitive to steric effects and takes place in 2-amino-1-methylpyrrole at C-5 and the exo amino group but at C-3 in 2-amino-1-t-butylpyrrole.

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U2 - 10.1016/j.tetlet.2007.04.036

DO - 10.1016/j.tetlet.2007.04.036

M3 - Article

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SN - 0040-4039

VL - 48

SP - 3991

EP - 3994

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Effect of the leaving group on the reaction of 2-aminopyrroles with electron deficient heteroaromatic azadienes: substitution by addition-elimination versus cycloaddition

Abstract

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