Literature DB >> 27688484

A General Method for Nucleophilic Aromatic Substitution of Aryl Fluorides and Chlorides with Dimethylamine using Hydroxide-Assisted Decomposition of N,N-Dimethylforamide.

Juana Garcia1, Jacob Sorrentino1, Emily J Diller1, Daniel Chapman1, Zachary R Woydziak1.   

Abstract

A practical and convenient procedure for the nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine was developed using a hydroxide assisted, thermal decomposition of N,N-dimethylforamide. These conditions are tolerant of nitro, nitrile, aldehyde, ketone, and amide groups but will undergo acyl substitution to form amides for methyl esters and acyl chlorides. Isolated yields of the products range from 44 - 98%, with the majority being greater than 70% for seventeen examples.

Entities:  

Keywords:  DMF decomposition; Nucleophilic Aromatic Substitution; aniline derivatives; aryl halides; dimethylamine

Year:  2016        PMID： 27688484      PMCID： PMC5036528          DOI： 10.1080/00397911.2016.1147051

Source DB:  PubMed          Journal:  Synth Commun        ISSN： 0039-7911            Impact factor:   2.007


  15 in total

1.  Hydrophobicity and central nervous system agents: on the principle of minimal hydrophobicity in drug design.

Authors:  C Hansch; J P Björkroth; A Leo
Journal:  J Pharm Sci       Date:  1987-09       Impact factor: 3.534

2.  Induction of angiotensin II subtype 2 receptor-mediated blood pressure regulation in synthetic diet-fed rats.

Authors:  M Tamura; T Takagi; E F Howard; E J Landon; A Steimle; M Tanner; P R Myers
Journal:  J Hypertens       Date:  2000-09       Impact factor: 4.844

3.  2,3-Diaminopyrazines as Rho kinase inhibitors.

Authors:  Alan J Henderson; Mark Hadden; Cheng Guo; Neema Douglas; Helene Decornez; Mark R Hellberg; Andrew Rusinko; Marsha McLaughlin; Naj Sharif; Colene Drace; Raj Patil
Journal:  Bioorg Med Chem Lett       Date:  2009-12-05       Impact factor: 2.823

4.  Selective progesterone receptor modulators in reproductive medicine: pharmacology, clinical efficacy and safety.

Authors:  Philippe Bouchard; Nathalie Chabbert-Buffet; Bart C J M Fauser
Journal:  Fertil Steril       Date:  2011-09-23       Impact factor: 7.329

Review 5.  G-quadruplex interacting small molecules and drugs: from bench toward bedside.

Authors:  Sebastian Müller; Raphaël Rodriguez
Journal:  Expert Rev Clin Pharmacol       Date:  2014-08-04       Impact factor: 5.045

6.  Synthesis and structure-activity relationships of a novel series of non-peptide angiotensin II receptor binding inhibitors specific for the AT2 subtype.

Authors:  C J Blankley; J C Hodges; S R Klutchko; R J Himmelsbach; A Chucholowski; C J Connolly; S J Neergaard; M S Van Nieuwenhze; A Sebastian; J Quin
Journal:  J Med Chem       Date:  1991-11       Impact factor: 7.446

7.  Orthoformimycin, a selective inhibitor of bacterial translation elongation from Streptomyces containing an unusual orthoformate.

Authors:  Sonia I Maffioli; Attilio Fabbretti; Letizia Brandi; Andreas Savelsbergh; Paolo Monciardini; Monica Abbondi; Rossana Rossi; Stefano Donadio; Claudio O Gualerzi
Journal:  ACS Chem Biol       Date:  2013-08-15       Impact factor: 5.100

8.  Dimethylformamide as a carbon monoxide source in fast palladium-catalyzed aminocarbonylations of aryl bromides.

Authors:  Yiqian Wan; Mathias Alterman; Mats Larhed; Anders Hallberg
Journal:  J Org Chem       Date:  2002-08-23       Impact factor: 4.354

9.  Potential antitumor agents. 61. Structure-activity relationships for in vivo colon 38 activity among disubstituted 9-oxo-9H-xanthene-4-acetic acids.

Authors:  G W Rewcastle; G J Atwell; Z A Li; B C Baguley; W A Denny
Journal:  J Med Chem       Date:  1991-01       Impact factor: 7.446

Review 10.  Doxycycline and Tigecycline: Two Friendly Drugs with a Low Association with Clostridium Difficile Infection.

Authors:  Yuan-Pin Hung; Jen-Chieh Lee; Hsiao-Ju Lin; Hsiao-Chieh Liu; Yi-Hui Wu; Pei-Jane Tsai; Wen-Chien Ko
Journal:  Antibiotics (Basel)       Date:  2015-06-19
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  2 in total

1.  Synthesis of Rhodamines and Rosamines Using 3,6-Difluoroxanthone as a Common Intermediate.

Authors:  Carlos Arambula; Joseph Rodrigues; Jung Jae Koh; Zachary Woydziak
Journal:  J Org Chem       Date:  2021-11-24       Impact factor: 4.354

2.  Stabilising fleeting intermediates of stilbene photocyclization with amino-borane functionalisation: the rare isolation of persistent dihydrophenanthrenes and their [1,5] H-shift isomers.

Authors:  Yong-Gang Shi; Soren K Mellerup; Kang Yuan; Guo-Fei Hu; Francoise Sauriol; Tai Peng; Nan Wang; Pangkuan Chen; Suning Wang
Journal:  Chem Sci       Date:  2018-03-27       Impact factor: 9.825
  2 in total

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