Literature DB >> 22482705

Reductive N-alkylation of nitroarenes: a green approach for the N-alkylation of natural products.

Amir E Wahba1, Mark T Hamann.   

Abstract

A simple, mild, cost-effective, and green approach for the reductive mono-N-alkylation of nitroarenes has been developed. HOAc/Zn are utilized as the reducing system together with a carbonyl compound as an alkyl source in methanol. Excellent yields were obtained with stoichiometric control of mono- over dialkylated products. Application to five complex natural products demonstrated the practical utility of the method.

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Year:  2012        PMID： 22482705      PMCID： PMC4883703          DOI： 10.1021/jo300303d

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


  23 in total

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Authors:  K C Nicolaou; Tamsyn Montagnon; Scott A Snyder
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2.  Antimalarial activity of a new family of analogues of manzamine A.

Authors:  Jeffrey D Winkler; Allyn T Londregan; Mark T Hamann
Journal:  Org Lett       Date:  2006-06-08       Impact factor: 6.005

3.  Borrowing hydrogen methodology for amine synthesis under solvent-free microwave conditions.

Authors:  Andrew J A Watson; Aoife C Maxwell; Jonathan M J Williams
Journal:  J Org Chem       Date:  2011-02-23       Impact factor: 4.354

4.  Synthesis and biological evaluation of manzamine analogues.

Authors:  Jeffrey D Winkler; Allyn T Londregan; Justin R Ragains; Mark T Hamann
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

5.  Spiroindolones, a potent compound class for the treatment of malaria.

Authors:  Matthias Rottmann; Case McNamara; Bryan K S Yeung; Marcus C S Lee; Bin Zou; Bruce Russell; Patrick Seitz; David M Plouffe; Neekesh V Dharia; Jocelyn Tan; Steven B Cohen; Kathryn R Spencer; Gonzalo E González-Páez; Suresh B Lakshminarayana; Anne Goh; Rossarin Suwanarusk; Timothy Jegla; Esther K Schmitt; Hans-Peter Beck; Reto Brun; Francois Nosten; Laurent Renia; Veronique Dartois; Thomas H Keller; David A Fidock; Elizabeth A Winzeler; Thierry T Diagana
Journal:  Science       Date:  2010-09-03       Impact factor: 47.728

6.  In situ hydrogen from aqueous-methanol for nitroarene reduction and imine formation over an Au-Pd/Al2O3 catalyst.

Authors:  Yizhi Xiang; Qiangqiang Meng; Xiaonian Li; Jianguo Wang
Journal:  Chem Commun (Camb)       Date:  2010-07-07       Impact factor: 6.222

7.  Structure-activity relationship studies of manzamine A: amidation of positions 6 and 8 of the beta-carboline moiety.

Authors:  Amir E Wahba; Jiangnan Peng; Sucheta Kudrimoti; Babu L Tekwani; Mark T Hamann
Journal:  Bioorg Med Chem       Date:  2009-09-19       Impact factor: 3.641

8.  2-N-Methyl modifications and SAR studies of manzamine A.

Authors:  Mohamed A Ibrahim; Abbas G Shilabin; Sivaprakasam Prasanna; Melissa Jacob; Shabana I Khan; Robert J Doerksen; Mark T Hamann
Journal:  Bioorg Med Chem       Date:  2008-06-05       Impact factor: 3.641

9.  Synthetic modification of manzamine A via Grubbs metathesis. Novel structures with enhanced antibacterial and antiprotozoal properties.

Authors:  Jeffrey D Winkler; Allyn T Londregan; Mark T Hamann
Journal:  Org Lett       Date:  2007-10-05       Impact factor: 6.005

10.  Semisynthetic studies on the manzamine alkaloids.

Authors:  Khalid A El Sayed; Ashraf A Khalil; Muhammad Yousaf; Guillermo Labadie; Gundluru M Kumar; Scott G Franzblau; Alejandro M S Mayer; Mitchell A Avery; Mark T Hamann
Journal:  J Nat Prod       Date:  2008-01-17       Impact factor: 4.050
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  1 in total

Review 1.  Catalytic Reductive Amination of Aldehydes and Ketones With Nitro Compounds: New Light on an Old Reaction.

Authors:  Alexey Yu Sukhorukov
Journal:  Front Chem       Date:  2020-04-15       Impact factor: 5.221
  1 in total

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