Rh-Catalyzed Reactions of 3-Diazoindolin-2-imines: Synthesis of Pyridoindoles and Tetrahydrofuropyrroloindoles

Organic Letters
Chen WangYanguang Wang

Abstract

The rhodium-catalyzed reactions of 3-diazoindolin-2-imines with furans and dihydrofuran furnished 9H-pyrido[2,3-b]indoles and tetrahydrofuro[3',2':4,5]pyrrolo[2,3-b]indoles, respectively. A cascade reaction mechanism involving an α-imino rhodium carbene intermediate is proposed. The starting materials are readily available, and the procedure is facile and efficient.

References

Oct 28, 2003·Angewandte Chemie·Anthony W G BurgettPatrick G Harran
Jul 14, 2006·Chemical Reviews·Guy R Humphrey, Jeffrey T Kuethe
Oct 16, 2008·Journal of the American Chemical Society·Tony HorneffValery V Fokin
Mar 12, 2009·Chemical Communications : Chem Comm·Tomoya MiuraMasahiro Murakami
Dec 1, 2009·Angewandte Chemie·Marco Bandini, Astrid Eichholzer
Feb 6, 2010·Journal of the American Chemical Society·Neil GrimsterValery V Fokin
Apr 13, 2010·Chemical Reviews·Anna J Kochanowska-Karamyan, Mark T Hamann
Sep 15, 2010·Natural Product Reports·Minoru IshikuraTakumi Abe
May 12, 2011·Chemical Reviews·Sandro Cacchi, Giancarlo Fabrizi
Jun 23, 2011·Organic Letters·Buddhadeb Chattopadhyay, Vladimir Gevorgyan
Nov 29, 2011·Angewandte Chemie·Buddhadeb Chattopadhyay, Vladimir Gevorgyan
Mar 7, 2012·Chemical Reviews·Morteza Shiri
Jul 24, 2012·Bioorganic & Medicinal Chemistry·Jing Lu LiangYurngdong Jahng
Dec 21, 2012·Angewandte Chemie·Mikhail Zibinsky, Valery V Fokin
Jan 9, 2013·Angewandte Chemie·Anton V Gulevich, Vladimir Gevorgyan
Mar 13, 2013·Journal of the American Chemical Society·Brendan T ParrHuw M L Davies
Mar 13, 2013·Journal of the American Chemical Society·Erica E Schultz, Richmond Sarpong
Apr 24, 2013·Journal of the American Chemical Society·Jillian E Spangler, Huw M L Davies
Jan 21, 2014·Journal of the American Chemical Society·Tomoya MiuraMasahiro Murakami
Mar 22, 2014·Bioorganic & Medicinal Chemistry Letters·Kazem Ahmed MahmoudAndreas Hilgeroth
May 8, 2014·Chemical Society Reviews·Huw M L Davies, Joshua S Alford
Oct 16, 2014·Chemical Society Reviews·Renato Dalpozzo
Dec 17, 2014·European Journal of Medicinal Chemistry·Andrew D WadsworthMargaret A Brimble

❮ Previous
Next ❯

Citations


❮ 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.