Literature DB >> 16555821

N,N-bond-forming heterocyclization: synthesis of 3-alkoxy-2H-indazoles.

Aaron D Mills1, Musa Z Nazer, Makhluf J Haddadin, Mark J Kurth.   

Abstract

A one-step heterocyclization of o-nitrobenzylamines to 3-alkoxy-2H-indazoles is reported. The electronic nature of the nitrophenyl group, the steric and electronic nature of the R1-functionalized benzylic amine, and the nature of the alcoholic solvent affect the efficiency of this heterocyclization reaction (approximately 40-90%).

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Year:  2006        PMID： 16555821     DOI： 10.1021/jo0524831

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

1.  Inhibition of myeloperoxidase: evaluation of 2H-indazoles and 1H-indazolones.

Authors:  Aaron Roth; Sean Ott; Kelli M Farber; Teresa A Palazzo; Wayne E Conrad; Makhluf J Haddadin; Dean J Tantillo; Carroll E Cross; Jason P Eiserich; Mark J Kurth
Journal:  Bioorg Med Chem       Date:  2014-10-02       Impact factor: 3.641

2.  Davis-Beirut Reaction: Diverse Chemistries of Highly Reactive Nitroso Intermediates in Heterocycle Synthesis.

Authors:  Jie S Zhu; Makhluf J Haddadin; Mark J Kurth
Journal:  Acc Chem Res       Date:  2019-07-22       Impact factor: 22.384

3.  The Davis-Beirut reaction: N1,N2-disubstituted-1H-indazolones via 1,6-electrophilic addition to 3-alkoxy-2H-indazoles.

Authors:  Wayne E Conrad; Ryo Fukazawa; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2011-05-25       Impact factor: 6.005

4.  A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles.

Authors:  Wayne E Conrad; Kevin X Rodriguez; Huy H Nguyen; James C Fettinger; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2012-07-23       Impact factor: 6.005

5.  Facile syntheses of novel benzo-1,3-dioxolo-, benzothiazolo-, pyrido-, and quinolino-fused 5H-benzo[d]-pyrazolo[5,1-b][1,3]-oxazines and 1H-pyrazoles.

Authors:  Belem Avila; Danielle M Solano; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2011-02-04       Impact factor: 6.005

6.  Davis-Beirut Reaction: A Photochemical Brønsted Acid Catalyzed Route to N-Aryl 2H-Indazoles.

Authors:  Niklas Kraemer; Clarabella J Li; Jie S Zhu; Julio M Larach; Ka Yi Tsui; Dean J Tantillo; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2019-07-24       Impact factor: 6.005

7.  Acid and base catalyzed Davis-Beirut reaction: experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles.

Authors:  Belem Avila; Mohammad H El-Dakdouki; Musa Z Nazer; Jason G Harrison; Dean J Tantillo; Makhluf J Haddadin; Mark J Kurth
Journal:  Tetrahedron Lett       Date:  2012-09-15       Impact factor: 2.415

8.  Davis-Beirut Reaction Inspired Nitroso Diels-Alder Reaction.

Authors:  Jung-Ho Son; Amy Cheung; Jie S Zhu; Makhluf J Haddadin; Mark J Kurth
Journal:  Tetrahedron Lett       Date:  2021-02-23       Impact factor: 2.415

9.  When biomolecules meet 2-hydrazinopyrazine: from theory through experiment to molecular levels using a wide spectrum of techniques.

Authors:  Paulina Mech; Mariusz Makowski; Anna Kawiak; Agnieszka Chylewska
Journal:  RSC Adv       Date:  2020-11-09       Impact factor: 4.036

10.  Davis-Beirut reaction: route to thiazolo-, thiazino-, and thiazepino-2H-indazoles.

Authors:  Kelli M Farber; Makhluf J Haddadin; Mark J Kurth
Journal:  J Org Chem       Date:  2014-07-23       Impact factor: 4.354
  10 in total

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