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'

Research output: Contribution to journalArticle

9 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3991-3994
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number23
DOIs
StatePublished - Jun 4 2007

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Cycloaddition
Cycloaddition Reaction
Substitution reactions
Electrons
N-methylpyrrole

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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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.",
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Effect of the leaving group on the reaction of 2-aminopyrroles with electron deficient heteroaromatic azadienes : substitution by addition-elimination versus cycloaddition. / De Rosa, Michael; Arnold, David; Medved', Miroslav.

In: Tetrahedron Letters, Vol. 48, No. 23, 04.06.2007, p. 3991-3994.

Research output: Contribution to journalArticle

TY - JOUR

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

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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