One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S8, and Formamide

Taoda Shi, Lynn Kaneko, Michael Sandino, Ryan Busse, Mae Zhang, Damian Mason, Jason Machulis, Andrew J. Ambrose, Donna Zhang, Eli Chapman

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Thieno[2,3-d]pyrimidin-4(3H)-ones are important pharmacophores that have previously required a three-step synthesis with two chromatography steps. We herein report a green approach to the synthesis of this pharmacologically important class of compounds via a catalytic four-component reaction using a ketone, ethyl cyanoacetate, S8, and formamide. The reported reaction is characterized by step economy, reduced catalyst loading, and easy purification.

Original languageEnglish (US)
Pages (from-to)1524-1528
Number of pages5
JournalACS Sustainable Chemistry and Engineering
Volume7
Issue number1
DOIs
StatePublished - Jan 7 2019

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ketone
Ketones
chromatography
purification
catalyst
Chromatography
Purification
Catalysts
economy
ethyl cyanoacetate
formamide

Keywords

  • Catalytic multicomponent reaction
  • green chemistry
  • Thieno[2,3- d]pyrimidin-4(3 H)-ones

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment

Cite this

One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S8, and Formamide. / Shi, Taoda; Kaneko, Lynn; Sandino, Michael; Busse, Ryan; Zhang, Mae; Mason, Damian; Machulis, Jason; Ambrose, Andrew J.; Zhang, Donna; Chapman, Eli.

In: ACS Sustainable Chemistry and Engineering, Vol. 7, No. 1, 07.01.2019, p. 1524-1528.

Research output: Contribution to journalArticle

Shi, Taoda ; Kaneko, Lynn ; Sandino, Michael ; Busse, Ryan ; Zhang, Mae ; Mason, Damian ; Machulis, Jason ; Ambrose, Andrew J. ; Zhang, Donna ; Chapman, Eli. / One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S8, and Formamide. In: ACS Sustainable Chemistry and Engineering. 2019 ; Vol. 7, No. 1. pp. 1524-1528.
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AU - Sandino, Michael

AU - Busse, Ryan

AU - Zhang, Mae

AU - Mason, Damian

AU - Machulis, Jason

AU - Ambrose, Andrew J.

AU - Zhang, Donna

AU - Chapman, Eli

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