One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S                         8                         , and Formamide

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

doi:10.1021/acssuschemeng.8b05276

One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S ₈ , and Formamide

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

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

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, S ₈ , and formamide. The reported reaction is characterized by step economy, reduced catalyst loading, and easy purification.

Original language	English (US)
Pages (from-to)	1524-1528
Number of pages	5
Journal	ACS Sustainable Chemistry and Engineering
Volume	7
Issue number	1
DOIs	https://doi.org/10.1021/acssuschemeng.8b05276
State	Published - Jan 7 2019

Keywords

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

ASJC Scopus subject areas

General Chemistry
Environmental Chemistry
General Chemical Engineering
Renewable Energy, Sustainability and the Environment

Access to Document

10.1021/acssuschemeng.8b05276

Cite this

Shi, T., Kaneko, L., Sandino, M., Busse, R., Zhang, M., Mason, D., Machulis, J., Ambrose, A. J., Zhang, D. D., & Chapman, E. (2019). One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S ₈ , and Formamide ACS Sustainable Chemistry and Engineering, 7(1), 1524-1528. https://doi.org/10.1021/acssuschemeng.8b05276

One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S ₈ , and Formamide . / Shi, Taoda; Kaneko, Lynn; Sandino, Michael et al.
In: ACS Sustainable Chemistry and Engineering, Vol. 7, No. 1, 07.01.2019, p. 1524-1528.

Research output: Contribution to journal › Article › peer-review

Shi, T, Kaneko, L, Sandino, M, Busse, R, Zhang, M, Mason, D, Machulis, J, Ambrose, AJ, Zhang, DD & Chapman, E 2019, ' One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S ₈ , and Formamide ', ACS Sustainable Chemistry and Engineering, vol. 7, no. 1, pp. 1524-1528. https://doi.org/10.1021/acssuschemeng.8b05276

Shi T, Kaneko L, Sandino M, Busse R, Zhang M, Mason D et al. One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S ₈ , and Formamide ACS Sustainable Chemistry and Engineering. 2019 Jan 7;7(1):1524-1528. doi: 10.1021/acssuschemeng.8b05276

Shi, Taoda ; Kaneko, Lynn ; Sandino, Michael et al. / One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S ₈ , and Formamide In: ACS Sustainable Chemistry and Engineering. 2019 ; Vol. 7, No. 1. pp. 1524-1528.

@article{ed49008ee0c34599b7c9933d49e034ee,

title = " One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S 8 , and Formamide ",

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, S 8 , and formamide. The reported reaction is characterized by step economy, reduced catalyst loading, and easy purification.",

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

author = "Taoda Shi and Lynn Kaneko and Michael Sandino and Ryan Busse and Mae Zhang and Damian Mason and Jason Machulis and Ambrose, \{Andrew J.\} and Zhang, \{Donna D.\} and Eli Chapman",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2019",

month = jan,

day = "7",

doi = "10.1021/acssuschemeng.8b05276",

language = "English (US)",

volume = "7",

pages = "1524--1528",

journal = "ACS Sustainable Chemistry and Engineering",

issn = "2168-0485",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - One-Step Synthesis of Thieno[2,3- d]pyrimidin-4(3 H)-ones via a Catalytic Four-Component Reaction of Ketones, Ethyl Cyanoacetate, S 8 , and Formamide

AU - Shi, Taoda

AU - Kaneko, Lynn

AU - Sandino, Michael

AU - Busse, Ryan

AU - Zhang, Mae

AU - Mason, Damian

AU - Machulis, Jason

AU - Ambrose, Andrew J.

AU - Zhang, Donna D.

AU - Chapman, Eli

PY - 2019/1/7

Y1 - 2019/1/7

N2 - 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, S 8 , and formamide. The reported reaction is characterized by step economy, reduced catalyst loading, and easy purification.

AB - 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, S 8 , and formamide. The reported reaction is characterized by step economy, reduced catalyst loading, and easy purification.

KW - Catalytic multicomponent reaction

KW - Thieno[2,3- d]pyrimidin-4(3 H)-ones

KW - green chemistry

UR - https://www.scopus.com/pages/publications/85059649826

UR - https://www.scopus.com/inward/citedby.url?scp=85059649826&partnerID=8YFLogxK

U2 - 10.1021/acssuschemeng.8b05276

DO - 10.1021/acssuschemeng.8b05276

M3 - Article

AN - SCOPUS:85059649826

SN - 2168-0485

VL - 7

SP - 1524

EP - 1528

JO - ACS Sustainable Chemistry and Engineering

JF - ACS Sustainable Chemistry and Engineering

IS - 1

ER -