Use of cyclohexylisocyanide and methyl 2-isocyanoacetate as convertible isocyanides for microwave-assisted fluorous synthesis of 1,4-benzodiazepine-2,5-dione library.

Journal of Combinatorial Chemistry
Hongyu ZhouBing Yan

Abstract

A new protocol in which cyclohexylisocyanide and methyl 2-isocyanoacetate are used as convertible isocyanides for Ugi/de-Boc/cyclization/Suzuki synthesis of biaryl-substituted 1,4-benzodiazepine-2,5-diones has been developed. Ugi reactions of Boc-protected anthranilic acids, fluorous benzaldehydes, amines, and cyclohexylisocyanide or methyl 2-isocyanoacetate were carried out at room temperature. Microwave-promoted de-Boc/cyclization reactions afforded 1,4-benzodiazepine-2,5-diones (BZDs). Suzuki coupling reactions further derivatized the BZD ring by removing the fluorous tag and introducing the biaryl group. A thirty three-member biaryl-substituted BZD library containing four points of diversity was prepared by microwave-assisted solution-phase fluorous parallel synthesis.

References

Dec 13, 1996·The Journal of Organic Chemistry·Thomas A. Keating, Robert W. Armstrong
May 13, 2003·Journal of Combinatorial Chemistry·Peter EttmayerKlaus Weigand
Jan 16, 2004·Methods in Enzymology·Christopher HulmeAdrian L Smith
Jan 25, 2005·Bioorganic & Medicinal Chemistry Letters·Daniel J ParksTianbao Lu
Feb 18, 2005·Journal of Medicinal Chemistry·Bruce L GrasbergerRoger F Bone
Apr 25, 2006·Bioorganic & Medicinal Chemistry Letters·Juan Jose MaruganTianbao Lu
Sep 7, 2006·Journal of the American Chemical Society·Michael C Pirrung, Subir Ghorai
Sep 30, 2008·Journal of Combinatorial Chemistry·Pascal VerdiéJean Martinez
May 5, 2009·The Journal of Organic Chemistry·Michael C PirrungTannya R Ibarra-Rivera
Oct 8, 2009·Journal of Combinatorial Chemistry·Aifeng LiuBing Yan

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Citations

Feb 12, 2011·ACS Combinatorial Science·Erik FensterPaul R Hanson
Mar 12, 2016·The Journal of Organic Chemistry·Diana E Ramírez-OrnelasEduardo Peña-Cabrera
Jan 10, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Luis Prent-PeñalozaJulio Caballero
Mar 8, 2014·Beilstein Journal of Organic Chemistry·Gijs KoopmanschapRomano Va Orru
Jul 31, 2012·Chemical Communications : Chem Comm·Shaoyu Li, Jie Wu
Oct 28, 2011·Chemical Communications : Chem Comm·Abhishek SharmaErik Van der Eycken
Apr 27, 2021·Organic & Biomolecular Chemistry·Hassan FarhidAhmad Shaabani
Jul 24, 2012·Analytical Chemistry·Nicola MarchettiAlberto Cavazzini
Dec 24, 2014·Chemical Research in Toxicology·Yi ZhangBing Yan
Jul 31, 2013·ACS Combinatorial Science·Yi-Wen PanWei-Chieh Cheng
Oct 15, 2014·Journal of Medicinal Chemistry·Michael R McKeownJames E Bradner

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