Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols

Ilya V. Seregin, Alex W. Schammel, Vladimir Gevorgyan

Research output: Contribution to journalArticle

72 Citations (Scopus)

Abstract

Two complementary protocols for assembly of multisubstituted N-fused heterocycles have been developed. It was demonstrated that 1,3-disubstituted N-fused heterocycles, including indolizines, pyrroloquinoxalines, and pyrrolothiazoles can easily be synthesized via an exceptionally mild and efficient method involving a novel silver-catalyzed cycloizomerization of propargyl-containing heterocycles. Alternatively, 1,2-disubstituted heterocycles can be accessed through the novel cascade transformation involving an alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, stannyl, or germyl groups. This mild and simple method allows for selective and highly efficient synthesis of indolizines, pyrroloisoquinolines, pyrroloquinoxalines, pyrrolopyrazines, and pyrrolothiazoles.

Original languageEnglish (US)
Pages (from-to)6876-6883
Number of pages8
JournalTetrahedron
Volume64
Issue number29
DOIs
StatePublished - Jul 14 2008
Externally publishedYes

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Indolizines
Transition metals
Metals
Alkynes
Isomerization
Silver
Hydrogen

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols. / Seregin, Ilya V.; Schammel, Alex W.; Gevorgyan, Vladimir.

In: Tetrahedron, Vol. 64, No. 29, 14.07.2008, p. 6876-6883.

Research output: Contribution to journalArticle

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