Palladium-catalysed carbonylation of 4-substituted 2-iodoaniline derivatives: carbonylative cyclisation and aminocarbonylation

Péter Ács, Erno Müller, Gábor Rangits, T. Lóránd, L. Kollár

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

2-Iodoaniline derivatives were used as bifunctional substrates in palladium-catalysed carbonylation. Depending on the substituents, two types of compounds were synthesised: having methyl or hydrogen in 4-position 2-aryl-benzo[d][1,3]oxazin-4-one derivatives have been formed, chloro, bromo, cyano or nitro groups in the same position resulted in the formation of dibenzo[b,f][1,5]-diazocine-6,12-dione derivatives. In the presence of various primary and secondary amines (tert-butylamine, amino acid methyl esters) as N-nucleophiles 2-ketocarboxamides were obtained as major products in aminocarbonylation reaction with double carbon monoxide insertion.

Original languageEnglish
Pages (from-to)12051-12056
Number of pages6
JournalTetrahedron
Volume62
Issue number51
DOIs
Publication statusPublished - Dec 18 2006

Fingerprint

Carbonylation
Cyclization
Palladium
Carbon Monoxide
Hydrogen
Esters
Derivatives
Amino Acids
Nucleophiles
Substrates
2-iodobenzenamine
tert-butylamine

Keywords

  • Amino acid
  • Aminocarbonylation
  • Carbon monoxide
  • Cyclisation
  • Iodoaniline
  • Ketocarboxamide
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Palladium-catalysed carbonylation of 4-substituted 2-iodoaniline derivatives : carbonylative cyclisation and aminocarbonylation. / Ács, Péter; Müller, Erno; Rangits, Gábor; Lóránd, T.; Kollár, L.

In: Tetrahedron, Vol. 62, No. 51, 18.12.2006, p. 12051-12056.

Research output: Contribution to journalArticle

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AU - Lóránd, T.

AU - Kollár, L.

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AB - 2-Iodoaniline derivatives were used as bifunctional substrates in palladium-catalysed carbonylation. Depending on the substituents, two types of compounds were synthesised: having methyl or hydrogen in 4-position 2-aryl-benzo[d][1,3]oxazin-4-one derivatives have been formed, chloro, bromo, cyano or nitro groups in the same position resulted in the formation of dibenzo[b,f][1,5]-diazocine-6,12-dione derivatives. In the presence of various primary and secondary amines (tert-butylamine, amino acid methyl esters) as N-nucleophiles 2-ketocarboxamides were obtained as major products in aminocarbonylation reaction with double carbon monoxide insertion.

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KW - Cyclisation

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