6-Substituted-5H-pyrrolo[2,3-b]pyrazines via palladium-catalyzed heteroannulation from N-(3-chloropyrazin-2-yl)-methanesulfonamide and alkynes

Corey R. Hopkins, Nicola Collar

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

We herein report the efficient and convenient synthesis of 6-substituted-5H-pyrrolo[2,3-b]pyrazines. The reaction is a palladium-catalyzed heteroannulation process followed by deprotection to yield the desired pyrrolo[2,3-b]pyrazine substrates. The reaction starts with readily accessible N-(3-chloropyrazin-2-yl)-methanesulfonamide and commercially available terminal alkynes and works with aryl- and alkylalkynes.

Original languageEnglish (US)
Pages (from-to)8087-8090
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number43
DOIs
StatePublished - Oct 18 2004

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Pyrazines
Alkynes
Palladium
Substrates
methanesulfonamide

Keywords

  • 6-Substituted-5H-pyrrolo[2,3-b]pyrazine
  • Cyclization
  • Heteroannulation
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

6-Substituted-5H-pyrrolo[2,3-b]pyrazines via palladium-catalyzed heteroannulation from N-(3-chloropyrazin-2-yl)-methanesulfonamide and alkynes. / Hopkins, Corey R.; Collar, Nicola.

In: Tetrahedron Letters, Vol. 45, No. 43, 18.10.2004, p. 8087-8090.

Research output: Contribution to journalArticle

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N2 - We herein report the efficient and convenient synthesis of 6-substituted-5H-pyrrolo[2,3-b]pyrazines. The reaction is a palladium-catalyzed heteroannulation process followed by deprotection to yield the desired pyrrolo[2,3-b]pyrazine substrates. The reaction starts with readily accessible N-(3-chloropyrazin-2-yl)-methanesulfonamide and commercially available terminal alkynes and works with aryl- and alkylalkynes.

AB - We herein report the efficient and convenient synthesis of 6-substituted-5H-pyrrolo[2,3-b]pyrazines. The reaction is a palladium-catalyzed heteroannulation process followed by deprotection to yield the desired pyrrolo[2,3-b]pyrazine substrates. The reaction starts with readily accessible N-(3-chloropyrazin-2-yl)-methanesulfonamide and commercially available terminal alkynes and works with aryl- and alkylalkynes.

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