Literature DB >> 14986964

Theoretical evidence for oxygenated intermediates in the reductive cyclization of nitrobenzenes.

Ian W Davies1, Vildan A Guner, K N Houk.   

Abstract

Deoxygenation of nitroaromatics is a classic synthetic method for the construction of nitrogen heterocycles. The generally accepted mechanism involves exhaustive deoxygenation to a singlet nitrene. We present theoretical evidence for an alternative, 6pi-electron 5-atom electrocyclization of nitroso-styrenes, -stilbenes, and -biphenyls to nitronates. A downstream 1,5-H shift and tautomerization leads to N-hydroxy heterocycles. [reaction: see text]

Entities:  

Year:  2004        PMID： 14986964     DOI： 10.1021/ol0364273

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


  10 in total

1.  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

2.  The evolution of drug design at Merck Research Laboratories.

Authors:  Frank K Brown; Edward C Sherer; Scott A Johnson; M Katharine Holloway; Bradley S Sherborne
Journal:  J Comput Aided Mol Des       Date:  2016-11-23       Impact factor: 3.686

3.  Fe(II)-catalyzed amination of aromatic C-H bonds via ring opening of 2H-azirines: synthesis of 2,3-disubstituted indoles.

Authors:  Samaresh Jana; Mack D Clements; Barry K Sharp; Nan Zheng
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

4.  A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via PIII/PV═O Redox Cycling.

Authors:  Trevor V Nykaza; Tyler S Harrison; Avipsa Ghosh; Rachel A Putnik; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2017-05-10       Impact factor: 15.419

5.  Examination of the mechanism of Rh(2)(II)-catalyzed carbazole formation using intramolecular competition experiments.

Authors:  Benjamin J Stokes; Kathleen J Richert; Tom G Driver
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

6.  Tandem 6pi-electrocyclization and cycloaddition of nitrodienes to yield multicyclic nitroso acetals.

Authors:  Gardner S Creech; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

7.  Accessing Multiple Classes of 2 H-Indazoles: Mechanistic Implications for the Cadogan and Davis-Beirut Reactions.

Authors:  Jie S Zhu; Clarabella J Li; Ka Yi Tsui; Niklas Kraemer; Jung-Ho Son; Makhluf J Haddadin; Dean J Tantillo; Mark J Kurth
Journal:  J Am Chem Soc       Date:  2019-04-04       Impact factor: 15.419

8.  On the mechanism of nitrosoarene-alkyne cycloaddition.

Authors:  Andrea Penoni; Giovanni Palmisano; Yi-Lei Zhao; Kendall N Houk; Jerome Volkman; Kenneth M Nicholas
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419

9.  Biphilic Organophosphorus-Catalyzed Intramolecular Csp2-H Amination: Evidence for a Nitrenoid in Catalytic Cadogan Cyclizations.

Authors:  Trevor V Nykaza; Antonio Ramirez; Tyler S Harrison; Michael R Luzung; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2018-02-12       Impact factor: 15.419

10.  Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles.

Authors:  Yingwei Zhao; Haoran Zhu; Siyoung Sung; Donald J Wink; Joseph M Zadrozny; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-20       Impact factor: 16.823
  10 in total

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