Transition-metal-catalyst-free synthesis of anthranilic acid derivatives by transfer hydrogenative coupling of 2-nitroaryl methanols with alcohols/amines

Literature Information

Publication Date 2017-12-19
DOI 10.1039/C7OB02919E
Impact Factor 3.876
Authors

Shudi Zhang, Zhenda Tan, Biao Xiong, Huan Feng Jiang


View Original

Abstract

By using a transfer hydrogenative coupling strategy, we herein describe a new method for the efficient synthesis of anthranilic acid derivatives, a significantly important class of compounds with extensive applications in organic synthesis and the discovery of bioactive molecules, from 2-nitroaryl methanols and readily available alcohols/amines. The synthesis proceeds with the merits of no need for a transition metal catalyst, operational simplicity, broad substrate scope, good functional tolerance, and high step efficiency, which offers a useful alternative to access anthranilic acid derivatives.

Related Literature

Potential-induced phase transition of low-index Au single crystal surfaces in propylene carbonate solution

Youn-Geun Kim, Kazuhiro Sato, Junji Inukai, Kingo Itaya

2011-11-23 Paper

DOI: 10.1039/C2CP23171A

Iron phthalocyanine coated on single-walled carbon nanotubes composite for the oxygen reduction reaction in alkaline media

Guofa Dong, Meihua Huang, Lunhui Guan

2012-01-06 Communication

DOI: 10.1039/C2CP23718K

Catalytic reactions on neutral Rh oxide clusters more efficient than on neutral Rh clusters

Akira Yamada, Ken Miyajima, Fumitaka Mafuné

2012-02-02 Paper

DOI: 10.1039/C2CP24036J

Intermediates and kinetics for phenolgasification in supercritical water

Chad M. Huelsman, Phillip E. Savage

2011-12-22 Paper

DOI: 10.1039/C2CP23910H

Molecular dynamics calculation of molecular volumes and volumes of activation

J. Spooner, N. Boon, E. Deglint, E. Edwards, B. Yanciw, B. Patton, L. Thiele, P. Dance

2012-01-12 Paper

DOI: 10.1039/C2CP22949H

The interaction of His337 with the Mn4Ca cluster of photosystem II

Simon Petrie, Phillip Gatt, Robert Stranger, Ron J. Pace

2012-02-13 Paper

DOI: 10.1039/C2CP23935C

The steric effect of aromatic pendant groups and electrical bistability in π-stacked polymers for memory devices

Bin Zhang, Xudong Chen, Zhenguo Chi, Jin Yang, Jiemei Ou, Ming Qiu Zhang, Dehao Li, Dong Wang, Mingkai Liu, Juying Zhou

2012-02-13 Paper

DOI: 10.1039/C2CP23953A

Front cover

Cover

DOI: 10.1039/C2CP90002E

The electric field as a novel switch for uptake/release of hydrogen for storage in nitrogen doped graphene

Z. M. Ao, F. M. Peeters, S. Li

2011-11-21 Paper

DOI: 10.1039/C1CP23153G

You might also like

Compound Q&A

What are the main uses of (3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8)?

(3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8) is primari...

79066-03-8(3.beta.)-3-Hydroxy-...
Compound Q&A

What regulatory guidelines apply to 5-(aminomethyl)-2-methoxyphenol (CAS: 89702-89-6)?

5-(Aminomethyl)-2-methoxyphenol (CAS: 89702-89-6) is classified under GHS as a s...

89702-89-65-(aminomethyl)-2-me...
Compound Q&A

What is Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7)?

Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7) is a heterocyclic organic compo...

28981-13-7Thieno[2,3-c]pyridin...
Compound Q&A

Is 1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride (CAS: 1185311-28-7) safe?

1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride is generally ...

1185311-28-71-[(6-Methoxy-3-pyri...
Compound Q&A

What regulatory guidelines apply to [(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2)?

[(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2) is regulated und...

146404-58-2[(2E)-3-Phenyl-2-pro...
Compound Q&A

What regulatory guidelines apply to 6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7)?

6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7) falls under the scope of the Glob...

1620515-86-76-Bromo-7-methoxyqui...
Compound Q&A

What industries use (2R)-1-(1-Benzofuran-2-yl)-N-propyl-2-pentanamine (CAS: 260550-89-8)?

This compound is primarily used in the pharmaceutical industry for the developme...

260550-89-8(2R)-1-(1-Benzofuran...
1228013-15-71-Ethyl-7-[2-methyl-...
Compound Q&A

Are there alternatives to {5-(Acryloylamino)-2-[(dimethylamino)methyl]phenyl}boronic acid (CAS: 1217500-78-1) in synthesis?

Alternative reagents such as 2-[(dimethylamino)methyl]phenylboronic acid or rela...

1217500-78-1{5-(Acryloylamino)-2...
Compound Q&A

What is 3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2)?

3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2) is an organic compound with the...

310881-48-23-(Piperidin-4-yloxy...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.