Literature DB >> 23180891

Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines.

Arthur Y Shaw1, Christine R Denning, Christopher Hulme.   

Abstract

A facile and expeditious synthetic approach to α-ketoamides 3 is described. A series of α-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of α-ketoamides 3 from various arylglyoxals with cyclic and acyclic secondary amines.

Entities:  

Year:  2012        PMID: 23180891      PMCID: PMC3501738          DOI: 10.1016/j.tetlet.2012.05.136

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


  13 in total

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Authors:  Antonio Garrido Montalban; Erik Boman; Chau-Dung Chang; Susana Conde Ceide; Russell Dahl; David Dalesandro; Nancy G J Delaet; Eric Erb; Justin T Ernst; Andrew Gibbs; Jeffrey Kahl; Linda Kessler; Jeff Kucharski; Christopher Lum; Jan Lundström; Stephen Miller; Hiroshi Nakanishi; Edward Roberts; Eddine Saiah; Robert Sullivan; Jan Urban; Zhijun Wang; Christopher J Larson
Journal:  Bioorg Med Chem Lett       Date:  2010-08-15       Impact factor: 2.823

2.  Trifluoromethylphenyl as P2 for ketoamide-based cathepsin S inhibitors.

Authors:  Jiaqiang Cai; John Robinson; Simone Belshaw; Kathryn Everett; Xavier Fradera; Mario van Zeeland; Leon van Berkom; Peter van Rijnsbergen; Lucy Popplestone; Mark Baugh; Maureen Dempster; John Bruin; William Hamilton; Emma Kinghorn; Paul Westwood; Jennifer Kerr; Zoran Rankovic; Wullie Arbuckle; D Jonathan Bennett; Philip S Jones; Clive Long; Iain Martin; Joost C M Uitdehaag; Tommi Meulemans
Journal:  Bioorg Med Chem Lett       Date:  2010-10-26       Impact factor: 2.823

3.  Structure-activity relationship of 2-oxoamide inhibition of group IVA cytosolic phospholipase A2 and group V secreted phospholipase A2.

Authors:  David A Six; Efrosini Barbayianni; Vassilios Loukas; Violetta Constantinou-Kokotou; Dimitra Hadjipavlou-Litina; Daren Stephens; Alan C Wong; Victoria Magrioti; Panagiota Moutevelis-Minakakis; Sharon F Baker; Edward A Dennis; George Kokotos
Journal:  J Med Chem       Date:  2007-08-02       Impact factor: 7.446

Review 4.  Chemistry and biology of the immunophilins and their immunosuppressive ligands.

Authors:  S L Schreiber
Journal:  Science       Date:  1991-01-18       Impact factor: 47.728

5.  Synthetic routes and lipase-inhibiting activity of long-chain alpha-keto amides.

Authors:  A Chiou; R Verger; G Kokotos
Journal:  Lipids       Date:  2001-05       Impact factor: 1.880

Review 6.  Peptidyl-prolyl isomerase inhibitors.

Authors:  Xiaodong J Wang; Felicia A Etzkorn
Journal:  Biopolymers       Date:  2006       Impact factor: 2.505

Review 7.  Synthetic inhibitors of elastase.

Authors:  P D Edwards; P R Bernstein
Journal:  Med Res Rev       Date:  1994-03       Impact factor: 12.944

8.  Potent ketoamide inhibitors of HCV NS3 protease derived from quaternized P1 groups.

Authors:  Srikanth Venkatraman; Francisco Velazquez; Wanli Wu; Melissa Blackman; Vincent Madison; F George Njoroge
Journal:  Bioorg Med Chem Lett       Date:  2010-02-14       Impact factor: 2.823

9.  Reactions of a carbamoylstannane with acid chlorides: highly efficient synthesis of alpha-oxo amides.

Authors:  Ruimao Hua; Hide-aki Takeda; Yoshimoto Abe; Masato Tanaka
Journal:  J Org Chem       Date:  2004-02-06       Impact factor: 4.354

10.  Novel 2-oxoamide inhibitors of human group IVA phospholipase A(2).

Authors:  George Kokotos; Stavroula Kotsovolou; David A Six; Violetta Constantinou-Kokotou; Christopher C Beltzner; Edward A Dennis
Journal:  J Med Chem       Date:  2002-07-04       Impact factor: 7.446

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  1 in total

1.  Synthesis of isocoumarins with different substituted patterns via Passerini-aldol sequence.

Authors:  Guan-Hua Ma; Bo Jiang; Xing-Jun Tu; Yi Ning; Shu-Jiang Tu; Guigen Li
Journal:  Org Lett       Date:  2014-08-20       Impact factor: 6.005

  1 in total

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