Literature DB >> 22752658

Exploring a sulfone linker utilizing trimethyl aluminum as a cleavage reagent: solid-phase synthesis of sulfonamides and ureas.

Tsai-Wen Chung1, Chih-Hau Chen, Chu-Chung Lin, Hsien-Jen Wu, Chung-Ming Sun, Wen-Sheng Chung.   

Abstract

A novel and efficient cleavage reagent, trimethyl aluminum, for traceless sulfinate-functionalized resin has been developed. The synthesis of sulfonamide and urea derivatives via a traceless solid-phase sulfone linker strategy through six synthetic steps comprising utilization of trimethyl aluminum as a novel cleavage reagent was also established. An insight of the plausible mechanism of the cleavage reaction was discussed.

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Year:  2012        PMID： 22752658     DOI： 10.1007/s11030-012-9380-3

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  39 in total

Review 1.  Traceless and multifunctional linkers for the generation of small molecules on solid supports.

Authors:  Carmen Gil; Stefan Bräse
Journal:  Curr Opin Chem Biol       Date:  2004-06       Impact factor: 8.822

2.  Polymer-supported (2,6-dichloro- 4-alkoxyphenyl)(2,4-dichlorophenyl)methanol: a new linker for solid-phase organic synthesis.

Authors:  Michio Kurosu; Kallolmay Biswas; Dean C Crick
Journal:  Org Lett       Date:  2007-02-21       Impact factor: 6.005

3.  Aluminum- and boron-mediated c-glycoside synthesis from 1,2-anhydroglycosides.

Authors:  J D Rainier; J M Cox
Journal:  Org Lett       Date:  2000-08-24       Impact factor: 6.005

4.  Synthesis of polymer-bound 4-acetoxy-3-phenylbenzaldehyde derivatives: applications in solid-phase organic synthesis.

Authors:  Anil Kumar; Guofeng Ye; Yousef Ahmadibeni; Keykavous Parang
Journal:  J Org Chem       Date:  2006-09-29       Impact factor: 4.354

5.  Tandem reaction of propargylic alcohol, sulfonamide, and N-iodosuccinimide: synthesis of N-(2-iodoinden-1-yl)arenesulfonamide.

Authors:  Yuanxun Zhu; Guangwei Yin; Deng Hong; Ping Lu; Yanguang Wang
Journal:  Org Lett       Date:  2011-01-26       Impact factor: 6.005

6.  Solid-phase synthesis of novel isoxazolocyclobutanones and isoxazolinocyclobutenones.

Authors:  Wei-Chieh Cheng; Melissa Wong; Marilyn M Olmstead; Mark J Kurth
Journal:  Org Lett       Date:  2002-03-07       Impact factor: 6.005

7.  Design, synthesis, crystal structures, and antimicrobial activity of sulfonamide boronic acids as β-lactamase inhibitors.

Authors:  Oliv Eidam; Chiara Romagnoli; Emilia Caselli; Kerim Babaoglu; Denise Teotico Pohlhaus; Joel Karpiak; Richard Bonnet; Brian K Shoichet; Fabio Prati
Journal:  J Med Chem       Date:  2010-11-11       Impact factor: 7.446

8.  Ionic liquid-supported (ILS) (S)-pyrrolidine sulfonamide, a recyclable organocatalyst for the highly enantioselective Michael addition to nitroolefins.

Authors:  Bukuo Ni; Qianying Zhang; Kritanjali Dhungana; Allan D Headley
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

9.  Identification of N-(5-tert-butyl-isoxazol-3-yl)-N'-{4-[7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea dihydrochloride (AC220), a uniquely potent, selective, and efficacious FMS-like tyrosine kinase-3 (FLT3) inhibitor.

Authors:  Qi Chao; Kelly G Sprankle; Robert M Grotzfeld; Andiliy G Lai; Todd A Carter; Anne Marie Velasco; Ruwanthi N Gunawardane; Merryl D Cramer; Michael F Gardner; Joyce James; Patrick P Zarrinkar; Hitesh K Patel; Shripad S Bhagwat
Journal:  J Med Chem       Date:  2009-12-10       Impact factor: 7.446

10.  Solid-phase synthesis of a thymidinyl dipeptide urea library.

Authors:  Dianqing Sun; Richard E Lee
Journal:  J Comb Chem       Date:  2007-04-07
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