Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines

Ming-Chang P. Yeh, Chia Jung Liang, Hsiao Feng Chen, Yu Ting Weng

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.

Original languageEnglish
Pages (from-to)3242-3254
Number of pages13
JournalAdvanced Synthesis and Catalysis
Volume357
Issue number14-15
DOIs
Publication statusPublished - 2015 Oct 1

Fingerprint

Indenes
Bearings (structural)
2-Naphthylamine
Pyridines
Indium
Cyclization
Pyridine
Gems
Derivatives

Keywords

  • amides
  • bromine
  • cyclization
  • indium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides : Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines. / Yeh, Ming-Chang P.; Liang, Chia Jung; Chen, Hsiao Feng; Weng, Yu Ting.

In: Advanced Synthesis and Catalysis, Vol. 357, No. 14-15, 01.10.2015, p. 3242-3254.

Research output: Contribution to journalArticle

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