A One-Step, Atom Economical Synthesis of Thieno[2,3-d]pyrimidin-4-amine Derivatives by a Four-Component Reaction

Taoda Shi, Christopher J. Zerio, Jared Sivinski, Andrew J. Ambrose, Kohlson T. Moore, Thomas Buckley, Lynn Kaneko, Mae Zhang, Donna Zhang, Eli Chapman

Research output: Contribution to journalArticle

Abstract

A Na2HPO4-catalyzed four-component reaction between a ketone, malononitrile, S8 and formamide has been realized for the first time. This reaction provides a concise approach to thieno[2,3-d]pyrimidin-4-amines, previously requiring 5 steps. The utility of this reaction was validated by preparing a multi-targeted kinase inhibitor and an inhibitor of the NRF2 pathway with excellent atom- and step-economy.

Original languageEnglish (US)
Pages (from-to)3269-3272
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number20
DOIs
StatePublished - Jun 2 2019

Fingerprint

Ketones
Amines
amines
Phosphotransferases
Derivatives
Atoms
inhibitors
synthesis
malononitrile
atoms
economy
ketones
dicyanmethane
formamide

Keywords

  • Atom economy
  • Multi-component reaction
  • Organocatalysis
  • Structural diversity
  • Thieno[2,3-d]pyrimidin-4-amines

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

A One-Step, Atom Economical Synthesis of Thieno[2,3-d]pyrimidin-4-amine Derivatives by a Four-Component Reaction. / Shi, Taoda; Zerio, Christopher J.; Sivinski, Jared; Ambrose, Andrew J.; Moore, Kohlson T.; Buckley, Thomas; Kaneko, Lynn; Zhang, Mae; Zhang, Donna; Chapman, Eli.

In: European Journal of Organic Chemistry, Vol. 2019, No. 20, 02.06.2019, p. 3269-3272.

Research output: Contribution to journalArticle

Shi, Taoda ; Zerio, Christopher J. ; Sivinski, Jared ; Ambrose, Andrew J. ; Moore, Kohlson T. ; Buckley, Thomas ; Kaneko, Lynn ; Zhang, Mae ; Zhang, Donna ; Chapman, Eli. / A One-Step, Atom Economical Synthesis of Thieno[2,3-d]pyrimidin-4-amine Derivatives by a Four-Component Reaction. In: European Journal of Organic Chemistry. 2019 ; Vol. 2019, No. 20. pp. 3269-3272.
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AU - Ambrose, Andrew J.

AU - Moore, Kohlson T.

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AU - Kaneko, Lynn

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