Literature DB >> 31857792

A one-step, atom economical synthesis of thieno[2,3-d]pyrimidin-4-amine derivatives via a four-component reaction.

Taoda Shi1, Christopher J Zerio1, Jared Sivinski1, Andrew J Ambrose1, Kohlson T Moore1, Thomas Buckley1, Lynn Kaneko1, Mae Zhang1, Donna D Zhang1, Eli Chapman1.   

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.

Entities:  

Keywords:  atom economy; multi-component reaction; structural diversity; thieno[2,3-d]pyrimidin-4-amines

Year:  2019        PMID： 31857792      PMCID： PMC6922009          DOI： 10.1002/ejoc.201900414

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  16 in total

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Authors:  Alexander Dömling; Wei Wang; Kan Wang
Journal:  Chem Rev       Date:  2012-03-22       Impact factor: 60.622

2.  A Small Molecule Inhibits Deregulated NRF2 Transcriptional Activity in Cancer.

Authors:  Michael J Bollong; Hwayoung Yun; Lance Sherwood; Ashley K Woods; Luke L Lairson; Peter G Schultz
Journal:  ACS Chem Biol       Date:  2015-08-17       Impact factor: 5.100

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Authors:  Diego J Ramón; Miguel Yus
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4.  A new four-component reaction involving the Michael addition and the Gewald reaction, leading to diverse biologically active 2-aminothiophenes.

Authors:  Joice Thomas; Sampad Jana; Mahendra Sonawane; Bert Fiey; Jan Balzarini; Sandra Liekens; Wim Dehaen
Journal:  Org Biomol Chem       Date:  2017-05-10       Impact factor: 3.876

5.  Computer-aided identification, synthesis and evaluation of substituted thienopyrimidines as novel inhibitors of HCV replication.

Authors:  Marcella Bassetto; Pieter Leyssen; Johan Neyts; Mark M Yerukhimovich; David N Frick; Andrea Brancale
Journal:  Eur J Med Chem       Date:  2016-07-19       Impact factor: 6.514

6.  Diversity-oriented three-component reactions of diazo compounds with anilines and 4-oxo-enoates.

Authors:  Changcheng Jing; Dong Xing; Yu Qian; Taoda Shi; Yun Zhao; Wenhao Hu
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-03       Impact factor: 15.336

7.  Discovery of thienopyrimidine-based inhibitors of the human farnesyl pyrophosphate synthase--parallel synthesis of analogs via a trimethylsilyl ylidene intermediate.

Authors:  Chun-Yuen Leung; Adrienne M Langille; John Mancuso; Youla S Tsantrizos
Journal:  Bioorg Med Chem       Date:  2013-02-18       Impact factor: 3.641

8.  Unraveling the Prenylation-Cancer Paradox in Multiple Myeloma with Novel Geranylgeranyl Pyrophosphate Synthase (GGPPS) Inhibitors.

Authors:  Cyrus M Lacbay; Daniel D Waller; Jaeok Park; Mònica Gómez Palou; Félix Vincent; Xian Fang Huang; Viviane Ta; Albert M Berghuis; Michael Sebag; Youla S Tsantrizos
Journal:  J Med Chem       Date:  2018-07-25       Impact factor: 7.446

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

Authors:  Taoda Shi; Lynn Kaneko; Michael Sandino; Ryan Busse; Mae Zhang; Damian Mason; Jason Machulis; Andrew J Ambrose; Donna D Zhang; Eli Chapman
Journal:  ACS Sustain Chem Eng       Date:  2018-12-14       Impact factor: 8.198

10.  Diversity-oriented synthetic strategy for developing a chemical modulator of protein-protein interaction.

Authors:  Jonghoon Kim; Jinjoo Jung; Jaeyoung Koo; Wansang Cho; Won Seok Lee; Chanwoo Kim; Wonwoo Park; Seung Bum Park
Journal:  Nat Commun       Date:  2016-10-24       Impact factor: 14.919
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