Literature DB >> 17978763

Synthesis of novel N-(4-ethoxyphenyl) azetidin-2-ones and their oxidative N-deprotection by ceric ammonium nitrate.

Aliasghar Jarrahpour1, Maaroof Zarei.   

Abstract

It is shown that the N-(p-ethoxyphenyl) group on beta-lactams can be oxidatively removed by ceric ammonium nitrate in good yield. Fourteen new N-(p-ethoxyphenyl)-2-azetidinones 8a-n were synthesized through standard [2+2] ketene-imine cycloadditions (Staudinger reaction). Treatment of these compounds with ceric ammonium nitrate yielded the N-dearylated 2-azetidinones 9a-n in good to excellent yields. The effects of solvent, molar equiv of CAN and different temperatures have been investigated and optimum conditions were established.

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Year:  2007        PMID： 17978763      PMCID： PMC6149079          DOI： 10.3390/12102364

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  7 in total

1.  A convenient synthesis of quinones from hydroquinone dimethyl ethers. Oxidative demethylation with ceric ammonijm nitrate.

Authors:  P Jacob; P S Callery; A T Shulgin; N Castagnoli
Journal:  J Org Chem       Date:  1976-10-29       Impact factor: 4.354

2.  Nuclear analogues of beta-lactam antibiotics. 2 The total synthesis of 8-oxo-4-thia-z-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acids.

Authors:  D B Byran; R F Hall; K G Holden; W F Huffman; J G Gleason
Journal:  J Am Chem Soc       Date:  1977-03-30       Impact factor: 15.419

3.  Nuclear analogues of beta-lactam antibiotics. I. the total synthesis of a 7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid via a versatile monocyclic beta-lactam intermediate.

Authors:  W F Huffman; K G Holden; T F Buckley; J G Gleason; L Wu
Journal:  J Am Chem Soc       Date:  1977-03-30       Impact factor: 15.419

4.  Exploring a benzyloxyaniline linker utilizing ceric ammonium nitrate (CAN) as a cleavage reagent: solid-phase synthesis of N-unsubstituted beta-lactams and secondary amides.

Authors:  K H Gordon; S Balasubramanian
Journal:  Org Lett       Date:  2001-01-11       Impact factor: 6.005

5.  N-Thiolated beta-lactam antibacterials: effects of the N-organothio substituent on anti-MRSA activity.

Authors:  Bart Heldreth; Timothy E Long; Seyoung Jang; G Suresh Kumar Reddy; Edward Turos; Sonja Dickey; Daniel V Lim
Journal:  Bioorg Med Chem       Date:  2006-02-15       Impact factor: 3.641

6.  Synthesis of C-3' methyl taxotere (docetaxel).

Authors:  Christophe Lucatelli; Florian Viton; Yves Gimbert; Andrew E Greene
Journal:  J Org Chem       Date:  2002-12-27       Impact factor: 4.354

7.  Synthesis of novel N-sulfonyl monocyclic beta-lactams as potential antibacterial agents.

Authors:  Aliasghar Jarrahpour; Maaroof Zarei
Journal:  Molecules       Date:  2006-01-31       Impact factor: 4.411
  7 in total
  4 in total

1.  Synthesis of Oligosaccharide Components of the Outer Core Domain of P. aeruginosa Lipopolysaccharide Using a Multifunctional Hydroquinone-Derived Reducing-End Capping Group.

Authors:  Abhishek Vartak; Fatma M Hefny; Steven J Sucheck
Journal:  Org Lett       Date:  2017-12-29       Impact factor: 6.005

2.  2-[1-(4-Ethoxy-phen-yl)-2-oxo-4-styryl-azetidin-3-yl]isoindoline-1,3-dione.

Authors:  Mehmet Akkurt; Selvi Karaca; Ali Asghar Jarrahpour; Maaroof Zarei; Orhan Büyükgüngör
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-04-26

3.  Crystal structure of 3-(4-chloro-phen-oxy)-4-(2-nitro-phen-yl)azetidin-2-one with an unknown solvate.

Authors:  Sevim Türktekin Çelikesir; Mehmet Akkurt; Aliasghar Jarrahpour; Habib Allah Shafie; Ömer Çelik
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-01

4.  Direct Access to Substituted 4-CF3 β-Lactams at the C-3 Position.

Authors:  Monika Skibińska; Marcin Kaźmierczak; Thierry Milcent; Tomasz Cytlak; Henryk Koroniak; Benoit Crousse
Journal:  Front Chem       Date:  2019-08-06       Impact factor: 5.221
  4 in total

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