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Literature DB >> 20161580

An Efficient Boric Acid Mediated Preparation of α-Hydroxyamides.

J Sravan Kumar¹, Subash C Jonnalagadda, Venkatram R Mereddy.

Abstract

An efficient methodology for the preparation of α-hydroxyamides via boric acid mediated addition of isonitriles on to aldehydes has been developed. The reaction of isonitriles with α-boronobenzaldehyde takes place under intramolecular catalysis conditions to provide functionalized benzoxaboroles.

Entities: Chemical Disease

Year: 2010 PMID： 20161580 PMCID： PMC2808032 DOI： 10.1016/j.tetlet.2009.12.008

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

12 in total

1. Multicomponent Reactions with Isocyanides.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-09-15 Impact factor: 15.336

2. A heterobimetallic Ga/Yb-Schiff base complex for catalytic asymmetric alpha-addition of isocyanides to aldehydes.

Authors: Hisashi Mihara; Yingjie Xu; Nicholas E Shepherd; Shigeki Matsunaga; Masakatsu Shibasaki
Journal: J Am Chem Soc Date: 2009-06-24 Impact factor: 15.419

3. Lewis base catalyzed enantioselective aldol addition of acetaldehyde-derived silyl enol ether to aldehydes.

Authors: Scott E Denmark; Tommy Bui
Journal: J Org Chem Date: 2005-11-25 Impact factor: 4.354

4. Discovery of a new boron-containing antifungal agent, 5-fluoro-1,3-dihydro-1-hydroxy-2,1- benzoxaborole (AN2690), for the potential treatment of onychomycosis.

Authors: Stephen J Baker; Yong-Kang Zhang; Tsutomu Akama; Agnes Lau; Huchen Zhou; Vincent Hernandez; Weimin Mao; M R K Alley; Virginia Sanders; Jacob J Plattner
Journal: J Med Chem Date: 2006-07-27 Impact factor: 7.446

5. N-alkyl-4-boronopyridinium halides versus boric acid as catalysts for the esterification of alpha-hydroxycarboxylic acids.

Authors: Toshikatsu Maki; Kazuaki Ishihara; Hisashi Yamamoto
Journal: Org Lett Date: 2005-10-27 Impact factor: 6.005

6. Catalytic asymmetric Passerini-type reaction: chiral aluminum-organophosphate-catalyzed enantioselective alpha-addition of isocyanides to aldehydes.

Authors: Tao Yue; Mei-Xiang Wang; De-Xian Wang; Géraldine Masson; Jieping Zhu
Journal: J Org Chem Date: 2009-11-06 Impact factor: 4.354

7. Chiral salen-aluminum complex as a catalyst for enantioselective alpha-addition of isocyanides to aldehydes: asymmetric synthesis of 2-(1-hydroxyalkyl)-5-aminooxazoles.

Authors: Shi-Xin Wang; Mei-Xiang Wang; De-Xian Wang; Jieping Zhu
Journal: Org Lett Date: 2007-08-08 Impact factor: 6.005

8. Bradykinin B1 receptor antagonists: an alpha-hydroxy amide with an improved metabolism profile.

Authors: Scott D Kuduk; Ronald K Chang; Robert M Dipardo; Christina N Di Marco; Kathy L Murphy; Richard W Ransom; Duane R Reiss; Cuyue Tang; Thomayant Prueksaritanont; Douglas J Pettibone; Mark G Bock
Journal: Bioorg Med Chem Lett Date: 2008-08-05 Impact factor: 2.823

9. Discovery and structure-activity study of a novel benzoxaborole anti-inflammatory agent (AN2728) for the potential topical treatment of psoriasis and atopic dermatitis.

Authors: Tsutomu Akama; Stephen J Baker; Yong-Kang Zhang; Vincent Hernandez; Huchen Zhou; Virginia Sanders; Yvonne Freund; Richard Kimura; Kirk R Maples; Jacob J Plattner
Journal: Bioorg Med Chem Lett Date: 2009-03-09 Impact factor: 2.823

10. Design, synthesis and evaluation of novel hydroxyamides as orally available anticonvulsants.

Authors: Hilary A Schenck; Paul W Lenkowski; Indrani Choudhury-Mukherjee; Seong-Hoon Ko; James P Stables; Manoj K Patel; Milton L Brown
Journal: Bioorg Med Chem Date: 2004-03-01 Impact factor: 3.641

4 in total

1. Synthesis and evaluation of functionalized benzoboroxoles as potential anti-tuberculosis agents.

Authors: Mohammad A Alam; Kriti Arora; Shirisha Gurrapu; Sravan K Jonnalagadda; Grady L Nelson; Paul Kiprof; Subash C Jonnalagadda; Venkatram R Mereddy
Journal: Tetrahedron Date: 2016-03-17 Impact factor: 2.457

2. Development of Practical Methodologies for the Synthesis of Functionalized Benzoboroxoles.

Authors: J Sravan Kumar; Christopher M Bashian; Michael A Corsello; Subash C Jonnalagadda; Venkatram R Mereddy
Journal: Tetrahedron Lett Date: 2010-08-25 Impact factor: 2.415

3. Synthesis of triazolo-fused benzoxazepines and benzoxazepinones via Passerini reactions followed by 1,3-dipolar cycloadditions.

Authors: Fabio De Moliner; Martina Bigatti; Chiara De Rosa; Luca Banfi; Renata Riva; Andrea Basso
Journal: Mol Divers Date: 2014-06-04 Impact factor: 2.943

Review 4. The 100 facets of the Passerini reaction.

Authors: Luca Banfi; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva
Journal: Chem Sci Date: 2021-09-30 Impact factor: 9.825

4 in total