Ir(III)/MPAA-Catalyzed Mild and Selective C-H Amidation of N-Sulfonyl Ketimines: Access To Benzosultam-Fused Quinazolines/Quinazolinones

The Journal of Organic Chemistry
Aniket MishraIndubhusan Deb

Abstract

Ir(III)-catalyzed unprecedented mild C-H amidation for weakly coordinating cyclic N-sulfonyl ketimines, accelerated by a mono protected l-amino acid, has been developed. The method uses 1,4,2-dioxazol-5-ones as the robust amidating reagent in conjunction with a catalytic amount of silver triflate. It is highly selective and does not require a stoichiometric amount of oxidants or additives. A series of mechanistic experiments was performed to gain some insights into the reaction mechanism. The strategy provides easy access to novel benzosultam-quinazoline and benzosultam-quinazolinone hybrid scaffolds endowed with pharmaceutically relevant features.

References

Apr 23, 2008·Organic Letters·You-Qing WangYong-Gui Zhou
Dec 17, 2008·Bioorganic & Medicinal Chemistry Letters·Robert T HendricksSteven Swallow
Apr 18, 2009·European Journal of Medicinal Chemistry·Rondla RohiniVadde Ravinder
Apr 3, 2010·Journal of the American Chemical Society·Yi LuJin-Quan Yu
May 12, 2010·Bioorganic & Medicinal Chemistry Letters·L Nathan TumeyJohn J Harrington
Mar 8, 2012·Journal of the American Chemical Society·Takahiro NishimuraTamio Hayashi
Oct 16, 2012·European Journal of Medicinal Chemistry·Mohamed S A ElsayedKhaled A M Abouzid
Jan 29, 2013·Journal of the American Chemical Society·Takahiro NishimuraTamio Hayashi
Jun 12, 2013·Angewandte Chemie·Guoqiang Yang, Wanbin Zhang
Jan 20, 2015·Chemical Communications : Chem Comm·Shu-Tao MeiYe Wei
Mar 15, 2015·Journal of the American Chemical Society·Gang LiJin-Quan Yu
Sep 30, 2015·Journal of the American Chemical Society·Jie LiLutz Ackermann
Dec 24, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tebogo Ankie KhozaMalose Jack Mphahlele
May 12, 2016·Chemistry : a European Journal·Nagaraju BarsuBasker Sundararaju
Jun 25, 2016·The Journal of Organic Chemistry·Hui LiuJun Wang
Jul 14, 2016·The Journal of Organic Chemistry·Aniket MishraIndubhusan Deb
Aug 30, 2016·Journal of Medicinal Chemistry·Carlos M G AzevedoTrond Ulven
Jan 5, 2017·Chemical Reviews·Yoonsu ParkSukbok Chang
Jan 18, 2017·Organic & Biomolecular Chemistry·Raja K RitAkhila K Sahoo
Mar 16, 2017·Angewandte Chemie·Juhyeon ParkSukbok Chang
Apr 22, 2017·Chemical Communications : Chem Comm·Zheng LingWanbin Zhang
May 31, 2017·Chemistry : a European Journal·Yeongyu HwangSukbok Chang
Oct 27, 2017·The Journal of Organic Chemistry·Aniket MishraIndubhusan Deb

❮ Previous
Next ❯

Citations

Jun 7, 2018·Angewandte Chemie·Wusheng GuoArjan W Kleij
Sep 19, 2019·Chemistry, an Asian Journal·Tariq A ShahTharmalingam Punniyamurthy
Feb 20, 2020·Chemical Communications : Chem Comm·Biao YinQing Zhu
Jul 22, 2020·Organic & Biomolecular Chemistry·Writhabrata SarkarIndubhusan Deb
Feb 6, 2020·Organic & Biomolecular Chemistry·Payel GhoshAlakananda Hajra
Apr 9, 2019·Organic Letters·Jia-Wei LiMing-Hua Zeng
Jun 28, 2018·The Journal of Organic Chemistry·Gia L HoangJonathan A Ellman

❮ 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.