A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2 F2 -activated Tiemann rearrangement

Organic & Biomolecular Chemistry
Guofu ZhangChengrong Ding

Abstract

A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.

References

May 18, 2000·Organic Letters·Y q WuG S Hamilton
Jan 5, 2001·Journal of Medicinal Chemistry·J P FalgueyretM D Percival
May 29, 2002·Bioorganic & Medicinal Chemistry Letters·Tingwei CaiPeng George Wang
Oct 23, 2009·Chemical Society Reviews·Timothy NewhouseReinhard W Hoffmann
Jan 7, 2011·Nature·Katharine Sanderson
Oct 29, 2011·Chemical Society Reviews·Roger A Sheldon
Mar 1, 2012·Organic & Biomolecular Chemistry·Hosamani Basavaprabhu, Vommina V Sureshbabu
Dec 10, 2013·Organic Letters·Chen ZhuChuo Chen
Jan 16, 2014·Organic Letters·Chia-Chi LinTun-Cheng Chien
Jun 21, 2014·Chemical Communications : Chem Comm·Fan TengJiang Cheng
Aug 13, 2014·Angewandte Chemie·Jiajia DongK Barry Sharpless
Feb 11, 2015·The Journal of Organic Chemistry·Fan TengJiang Cheng
Jul 2, 2015·Journal of the American Chemical Society·Garazi TalaveraManuel Alcarazo
Jan 5, 2017·Journal of the American Chemical Society·Qian ZhaoJack Taunton
Jan 24, 2017·Journal of the American Chemical Society·Sydonie D SchimlerMelanie S Sanford
Apr 19, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·M R Ranga PrabhathPallavi Sharma
Jul 1, 2017·Organic Letters·James N AyresLouis C Morrill
Feb 1, 2016·Chemical Science·Yujiro Hayashi
Feb 17, 2018·Journal of the American Chemical Society·Zilei LiuPeng Wu
Jun 6, 2018·Organic & Biomolecular Chemistry·Zhen-Yuan LiaoTun-Cheng Chien
Jun 25, 2018·Bioorganic & Medicinal Chemistry Letters·Arthur F KlugeJames E Thompson
Jul 24, 2018·Chemistry : a European Journal·Karel ŠkochPetr Štěpnička
Nov 16, 2018·Journal of the American Chemical Society·Maxim EpifanovGlenn M Sammis
Nov 28, 2018·Journal of the American Chemical Society·Gao-Feng ZhaHua-Li Qin

❮ Previous
Next ❯

Citations

Aug 15, 2021·Chemistry : a European Journal·Zimin Chen, Weiming Yuan

❮ 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.