Synthesis of α-(4-Oxazolyl)amino Esters via Brønsted Acid Catalyzed Tandem Reaction

Organic Letters
Ansoo LeeHyunwoo Kim

Abstract

A one-step, Brønsted acid catalyzed tandem reaction for the synthesis of α-(4-oxazolyl)amino esters was developed. 4-Nitrobenzenesulfonic acid was found to be an efficient catalyst for the coupling of ethyl 2-oxobut-3-ynoates with amides to provide various α-(4-oxazolyl)amino esters. The experimental and X-ray crystallographic data suggest that a series of bond-forming reactions including imine formation, intermolecular Michael addition, and intramolecular Michael addition are involved to generate both the oxazole and amino acid functionalities.

References

Apr 23, 2002·Current Medicinal Chemistry·Celine Adessi, Claudio Soto
Aug 14, 2003·Chemical Reviews·Harald Gröger
Aug 14, 2003·Chemical Reviews·Keiji Maruoka, Takashi Ooi
Jul 9, 2004·Proceedings of the National Academy of Sciences of the United States of America·Tamas BartfaiJulius Rebek
Nov 24, 2004·Proceedings of the National Academy of Sciences of the United States of America·Susana Conde CeideJulius Rebek
Dec 16, 2004·Angewandte Chemie·Lei Wang, Peter G Schultz
Jul 31, 2007·Chemical Society Reviews·Jason S FiskJetze J Tepe
Oct 6, 2007·Chemical Reviews·Carmen Najera, José M Sansano
Nov 23, 2007·Bioorganic & Medicinal Chemistry Letters·John LiddleDeirdre M B Hickey
Oct 20, 2010·Chemical Reviews·Alexander M R Smith, King Kuok Mimi Hii
Aug 20, 2011·Chemical Reviews·Jun WangXiaoming Feng
Dec 21, 2012·Chemical Biology & Drug Design·David J CraikDavid Price
May 27, 2015·Chemical Communications : Chem Comm·Weiwei LuoXiaoming Feng
Aug 20, 2015·Bioconjugate Chemistry·Johnathan C MazaDouglas D Young
Feb 10, 2016·Journal of the American Chemical Society·Keisuke TokumasuTakashi Ohshima
Mar 31, 2017·Chemical Communications : Chem Comm·Kip A Teegardin, Jimmie D Weaver
Apr 6, 2018·Chemical Science·R A AycockN T Jui
Mar 2, 1998·Angewandte Chemie·Harald Dibowski, Franz P Schmidtchen

❮ Previous
Next ❯

Citations

Nov 20, 2019·Chemical Communications : Chem Comm·Kunhua XuXu Tian

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.