Base-Mediated [3 + 4]-Cycloaddition of Anthranils with Azaoxyallyl Cations: A New Approach to Multisubstituted Benzodiazepines

Organic Letters
Juan FengMing Zhao

Abstract

A new [3 + 4] cycloaddition of azaoxyallyl cations and anthranils has been achieved for rapid access to multisubstituted benzodiazepine derivatives. A variety of anthranils and α-halo hydroxamates were both effective substrates with simple operations under transition-metal-free conditions. The intriguing features of this method include its mild nature of the reaction conditions, high efficiency, broad substrate scope, and wide functional group compatibility.

References

Jan 1, 1979·Journal of Medicinal Chemistry·L H Sternbach
Feb 1, 1987·The Journal of Antibiotics·J E HochlowskiJ B McAlpine
Jul 8, 1999·Journal of Natural Products·L Rahbaek, J Breinholt
Feb 15, 2008·Medicinal Research Reviews·Masami Ishibashi, Takashi Ohtsuki
May 7, 2009·Drug Discovery Today·Allan M Jordan, Stephen D Roughley
May 4, 2011·Journal of the American Chemical Society·Christopher S JeffreyChristopher R Carson
Nov 8, 2012·Organic Letters·Christopher S JeffreyChristopher R Carson
Nov 13, 2015·Journal of the American Chemical Society·Arjun AcharyaChristopher Scott Jeffrey
Nov 13, 2015·Journal of the American Chemical Society·Maria C DiPotoJimmy Wu
Aug 4, 2016·Chemical Communications : Chem Comm·Yuanyuan AnJie Wu
Oct 20, 2018·Organic & Biomolecular Chemistry·Shaofa SunJian Wang
Nov 6, 2018·Chemical Society Reviews·Zengsheng YinPauline Chiu
Jul 2, 2019·The Journal of Organic Chemistry·Juan FengXuanzi Lin

❮ Previous
Next ❯

Citations

Sep 10, 2019·Organic & Biomolecular Chemistry·Abderrahman El BouakherSébastien Comesse
Sep 19, 2019·Chemistry, an Asian Journal·Tony RoyAkkattu T Biju

❮ 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.