Rhenium-catalyzed regioselective synthesis of multisubstituted pyridines from β-enamino ketones and alkynes via C-C bond cleavage

Shun Ichi Yamamoto, Kana Okamoto, Makiko Murakoso, Yoichiro Kuninobu, Kazuhiko Takai

Research output: Contribution to journalArticle

63 Citations (Scopus)

Abstract

A new method is described for the regioselective synthesis of multisubstituted pyridine derivatives. Treatment of N-acetyl β-enamino ketones with alkynes in the presence of the rhenium catalyst, Re 2(CO) 10, gives multisubstituted pyridines regioselectively. In this reaction, the N-acetyl moieties are important for the selective formation of the multisubstituted pyridines. This reaction proceeds via insertion of alkynes into a carbon-carbon single bond of β-enamino ketones, intramolecular nucleophilic cyclization, and elimination of acetic acid.

Original languageEnglish
Pages (from-to)3182-3185
Number of pages4
JournalOrganic Letters
Volume14
Issue number12
DOIs
Publication statusPublished - Jun 15 2012

Fingerprint

Rhenium
Pyridines
Alkynes
rhenium
alkynes
Ketones
ketones
cleavage
pyridines
Carbon
Cyclization
Carbon Monoxide
synthesis
Acetic Acid
carbon
Derivatives
acetic acid
Catalysts
insertion
elimination

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Rhenium-catalyzed regioselective synthesis of multisubstituted pyridines from β-enamino ketones and alkynes via C-C bond cleavage. / Yamamoto, Shun Ichi; Okamoto, Kana; Murakoso, Makiko; Kuninobu, Yoichiro; Takai, Kazuhiko.

In: Organic Letters, Vol. 14, No. 12, 15.06.2012, p. 3182-3185.

Research output: Contribution to journalArticle

Yamamoto, Shun Ichi ; Okamoto, Kana ; Murakoso, Makiko ; Kuninobu, Yoichiro ; Takai, Kazuhiko. / Rhenium-catalyzed regioselective synthesis of multisubstituted pyridines from β-enamino ketones and alkynes via C-C bond cleavage. In: Organic Letters. 2012 ; Vol. 14, No. 12. pp. 3182-3185.
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