Literature DB >> 18476707

Benzyne click chemistry: synthesis of benzotriazoles from benzynes and azides.

Feng Shi1, Jesse P Waldo, Yu Chen, Richard C Larock.   

Abstract

A variety of substituted benzotriazoles have been prepared by the [3 + 2] cycloaddition of azides to benzynes. The reaction scope is quite general, affording a rapid and easy entry to substituted, functionalized benzotriazoles under mild conditions.

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Year:  2008        PMID： 18476707      PMCID： PMC3750119          DOI： 10.1021/ol800675u

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  24 in total

1.  Facile insertion reaction of arynes into carbon-carbon sigma-bonds.

Authors:  Hiroto Yoshida; Masahiko Watanabe; Joji Ohshita; Atsutaka Kunai
Journal:  Chem Commun (Camb)       Date:  2005-06-01       Impact factor: 6.222

2.  Inhibitors of HIV-1 protease by using in situ click chemistry.

Authors:  Matthew Whiting; John Muldoon; Ying-Chuan Lin; Steven M Silverman; William Lindstrom; Arthur J Olson; Hartmuth C Kolb; M G Finn; K Barry Sharpless; John H Elder; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-20       Impact factor: 15.336

3.  Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates.

Authors:  Jian Zhao; Richard C Larock
Journal:  J Org Chem       Date:  2007-01-19       Impact factor: 4.354

4.  A new tandem reaction of benzyne: one-pot synthesis of aryl amines containing anthracene.

Authors:  Chunsong Xie; Yuhong Zhang
Journal:  Org Lett       Date:  2007-02-06       Impact factor: 6.005

5.  In situ click chemistry: a powerful means for lead discovery.

Authors:  K Barry Sharpless; Roman Manetsch
Journal:  Expert Opin Drug Discov       Date:  2006-11       Impact factor: 6.098

6.  The direct acyl-alkylation of arynes.

Authors:  Uttam K Tambar; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2005-04-20       Impact factor: 15.419

7.  An efficient, facile, and general synthesis of 1h-indazoles by 1,3-dipolar cycloaddition of arynes with diazomethane derivatives.

Authors:  Tienan Jin; Yoshinori Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  A 2:1 coupling reaction of arynes with aldehydes via o-quinone methides: straightforward synthesis of 9-arylxanthenes.

Authors:  Hiroto Yoshida; Masahiko Watanabe; Hiroyuki Fukushima; Joji Ohshita; Atsutaka Kunai
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

9.  Synthesis and activity of 1H-benzimidazole and 1H-benzotriazole derivatives as inhibitors of Acanthamoeba castellanii.

Authors:  Katarzyna Kopańska; Andzelika Najda; Justyna Zebrowska; Lidia Chomicz; Janusz Piekarczyk; Przemysław Myjak; Maria Bretner
Journal:  Bioorg Med Chem       Date:  2004-05-15       Impact factor: 3.641

10.  Transfer printing of DNA by "click" chemistry.

Authors:  Dorota I Rozkiewicz; Johannes Gierlich; Glenn A Burley; Katrin Gutsmiedl; Thomas Carell; Bart Jan Ravoo; David N Reinhoudt
Journal:  Chembiochem       Date:  2007-11-05       Impact factor: 3.164
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  31 in total

1.  Steric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes.

Authors:  Sarah M Bronner; Joel L Mackey; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2012-08-15       Impact factor: 15.419

2.  The Disappearing Director: The Case of Directed N-Arylation via a Removable Hydroxyl Group.

Authors:  Magdalena R Andrzejewska; Prasanna K Vuram; Narender Pottabathini; Venkateshwarlu Gurram; Siva Subrahmanyam Relangi; Kirill A Korvinson; Raju Doddipalla; Lothar Stahl; Michelle C Neary; Padmanava Pradhan; Somesh Sharma; Mahesh K Lakshman
Journal:  Adv Synth Catal       Date:  2018-04-16       Impact factor: 5.837

3.  Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones.

Authors:  Chunrui Wu; Yuesi Fang; Richard C Larock; Feng Shi
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

4.  Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.

Authors:  Tejas K Shah; Jose M Medina; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

5.  Overturning indolyne regioselectivities and synthesis of indolactam V.

Authors:  Sarah M Bronner; Adam E Goetz; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-02-25       Impact factor: 15.419

6.  Synthesis of benzisoxazoles by the [3 + 2] cycloaddition of in situ generated nitrile oxides and arynes.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

7.  Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions.

Authors:  G-Yoon J Im; Sarah M Bronner; Adam E Goetz; Robert S Paton; Paul H-Y Cheong; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2010-11-29       Impact factor: 15.419

8.  Synthesis of acridines by the [4 + 2] annulation of arynes and 2-aminoaryl ketones.

Authors:  Donald C Rogness; Richard C Larock
Journal:  J Org Chem       Date:  2010-04-02       Impact factor: 4.354

9.  Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

Authors:  John B Feltenberger; Ryuji Hayashi; Yu Tang; Eric S C Babiash; Richard P Hsung
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

10.  Modification of triclosan scaffold in search of improved inhibitors for enoyl-acyl carrier protein (ACP) reductase in Toxoplasma gondii.

Authors:  Jozef Stec; Alina Fomovska; Gustavo A Afanador; Stephen P Muench; Ying Zhou; Bo-Shiun Lai; Kamal El Bissati; Mark R Hickman; Patty J Lee; Susan E Leed; Jennifer M Auschwitz; Caroline Sommervile; Stuart Woods; Craig W Roberts; David Rice; Sean T Prigge; Rima McLeod; Alan P Kozikowski
Journal:  ChemMedChem       Date:  2013-06-14       Impact factor: 3.466
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