Literature DB >> 14870846

Efficient microwave assisted synthesis of optically active bicyclic 2-pyridinones via delta2-thiazolines.

Hans Emtenäs1, Camilla Taflin, Fredrik Almqvist.   

Abstract

A new efficient synthesis of optically active bicyclic 2-pyridiones has been developed using microwave irradiation. The synthesis is a two-step procedure via delta2-thiazolines, which only requires a 3 + 2 min reaction time compared to 2 days when using conventional heating. The optimized conditions proved to be suitable for the synthesis of a small library in excellent yields and with limited racemizations.

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Year:  2003        PMID： 14870846     DOI： 10.1023/b:modi.0000006800.46154.99

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


  8 in total

1.  Total synthesis and semi-synthetic approaches to analogues of antibacterial natural product althiomycin.

Authors:  Paola Zarantonello; Colin P Leslie; Rafael Ferritto; Wieslaw M Kazmierski
Journal:  Bioorg Med Chem Lett       Date:  2002-02-25       Impact factor: 2.823

Review 2.  High-speed combinatorial synthesis utilizing microwave irradiation.

Authors:  C Oliver Kappe
Journal:  Curr Opin Chem Biol       Date:  2002-06       Impact factor: 8.822

3.  Design and evaluation of pilicides: potential novel antibacterial agents directed against uropathogenic Escherichia coli.

Authors:  A Svensson; A Larsson; H Emtenäs; M Hedenström; T Fex; S J Hultgren; J S Pinkner; F Almqvist; J Kihlberg
Journal:  Chembiochem       Date:  2001-12-03       Impact factor: 3.164

Review 4.  Enhancement of combinatorial chemistry by microwave-assisted organic synthesis.

Authors:  Pelle Lidström; Jacob Westman; Anthony Lewis
Journal:  Comb Chem High Throughput Screen       Date:  2002-09       Impact factor: 1.339

5.  An enantioselective ketene-imine cycloaddition method for synthesis of substituted ring-fused 2-pyridinones.

Authors:  H Emtenäs; L Alderin; F Almqvist
Journal:  J Org Chem       Date:  2001-10-05       Impact factor: 4.354

6.  Design and parallel solid-phase synthesis of ring-fused 2-pyridinones that target pilus biogenesis in pathogenic bacteria.

Authors:  Hans Emtenäs; Kristoffer Ahlin; Jerome S Pinkner; Scott J Hultgren; Fredrik Almqvist
Journal:  J Comb Chem       Date:  2002 Nov-Dec

7.  Benzamide bioisosteres incorporating dihydroheteroazole substructures: EPC synthesis and SAR leading to a selective dopamine D4 receptor partial agonist (FAUC 179).

Authors:  J Einsiedel; H Hübner; P Gmeiner
Journal:  Bioorg Med Chem Lett       Date:  2001-09-17       Impact factor: 2.823

8.  Synthesis and biological evaluation of structurally highly modified analogues of the antimitotic natural product curacin A.

Authors:  Peter Wipf; Jonathan T Reeves; Raghavan Balachandran; Billy W Day
Journal:  J Med Chem       Date:  2002-04-25       Impact factor: 7.446
  8 in total
  9 in total

1.  Unusual light spectroscopic properties of a 2-pyridone-based multi-ring-fused fluorescent scaffold.

Authors:  Erik Rosenbaum; Magnus Sellstedt; Fredrik Almqvist; Lennart B-A Johansson
Journal:  J Fluoresc       Date:  2010-05-20       Impact factor: 2.217

Review 2.  One hundred years of Meldrum's acid: advances in the synthesis of pyridine and pyrimidine derivatives.

Authors:  Victoria V Lipson; Nikolay Yu Gorobets
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

3.  Synthesis and application of a bromomethyl substituted scaffold to be used for efficient optimization of anti-virulence activity.

Authors:  Erik Chorell; Christoffer Bengtsson; Thomas Sainte-Luce Banchelin; Pralay Das; Hanna Uvell; Arun K Sinha; Jerome S Pinkner; Scott J Hultgren; Fredrik Almqvist
Journal:  Eur J Med Chem       Date:  2011-01-21       Impact factor: 6.514

4.  Carboxylic acid isosteres improve the activity of ring-fused 2-pyridones that inhibit pilus biogenesis in E. coli.

Authors:  Veronica Berg; Pralay Das; Erik Chorell; Mattias Hedenström; Jerome S Pinkner; Scott J Hultgren; Fredrik Almqvist
Journal:  Bioorg Med Chem Lett       Date:  2008-05-07       Impact factor: 2.823

5.  Small-molecule inhibitors target Escherichia coli amyloid biogenesis and biofilm formation.

Authors:  Lynette Cegelski; Jerome S Pinkner; Neal D Hammer; Corinne K Cusumano; Chia S Hung; Erik Chorell; Veronica Aberg; Jennifer N Walker; Patrick C Seed; Fredrik Almqvist; Matthew R Chapman; Scott J Hultgren
Journal:  Nat Chem Biol       Date:  2009-10-25       Impact factor: 15.040

6.  Rationally designed small compounds inhibit pilus biogenesis in uropathogenic bacteria.

Authors:  Jerome S Pinkner; Han Remaut; Floris Buelens; Eric Miller; Veronica Aberg; Nils Pemberton; Mattias Hedenström; Andreas Larsson; Patrick Seed; Gabriel Waksman; Scott J Hultgren; Fredrik Almqvist
Journal:  Proc Natl Acad Sci U S A       Date:  2006-11-10       Impact factor: 11.205

7.  A selective intramolecular 5-exo-dig or 6-endo-dig cyclization en route to 2-furanone or 2-pyrone containing tricyclic scaffolds.

Authors:  Christoffer Bengtsson; Fredrik Almqvist
Journal:  J Org Chem       Date:  2011-10-31       Impact factor: 4.354

Review 8.  Small Molecule Anti-biofilm Agents Developed on the Basis of Mechanistic Understanding of Biofilm Formation.

Authors:  Katrine Qvortrup; Louise Dahl Hultqvist; Martin Nilsson; Tim Holm Jakobsen; Charlotte Uldahl Jansen; Jesper Uhd; Jens Bo Andersen; Thomas E Nielsen; Michael Givskov; Tim Tolker-Nielsen
Journal:  Front Chem       Date:  2019-11-01       Impact factor: 5.221

9.  Asymmetric synthesis of 2,4,5-trisubstituted Δ2-thiazolines.

Authors:  Christoffer Bengtsson; Hanna Nelander; Fredrik Almqvist
Journal:  Chemistry       Date:  2013-06-17       Impact factor: 5.236
  9 in total

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