Tandem Thien- and benzannulations of α-alkenoyl-α-alkynyl ketene dithioacetals with cyanoacetates: synthesis of functionalized benzo[b]thiophenes

Organic Letters
Wenbo MingMang Wang

Abstract

A novel domino annulation strategy for the construction of benzo[b]thiophenes has been developed. In the presence of Cs2CO3 and Ag2CO3, a wide range of α-alkenoyl-α-alkynyl ketene dithioacetals readily react with cyanoacetates in CH3CN at 110 °C under N2 to afford multisubstituted benzo[b]thiophenes efficiently via tandem thien- and benzannulations. A plausible mechanism is also proposed.

References

May 31, 2002·Journal of Medicinal Chemistry·Bernard L FlynnM Katherine Jung
Jul 12, 2002·Chemical Communications : Chem Comm·Marie E MigaudChristopher J Schofield
Apr 3, 2003·Chemical Communications : Chem Comm·K C NicolaouScott A Snyder
Mar 31, 2005·Journal of the American Chemical Society·Xihe BiBing Li
Nov 1, 2006·Angewandte Chemie·K C NicolaouPaul G Bulger
May 11, 2007·Journal of Medicinal Chemistry·Zhihui QinGregory R J Thatcher
Oct 18, 2007·Tetrahedron·Albert Padwa, Scott K Bur
Jul 19, 2008·Chemical Reviews·Eloísa Jiménez-Núñez, Antonio M Echavarren
Dec 25, 2008·The Journal of Organic Chemistry·Saurabh MehtaRichard C Larock
Mar 20, 2009·The Journal of Organic Chemistry·Benjamin J StokesTom G Driver
Jul 3, 2009·Journal of Combinatorial Chemistry·Chul-Hee ChoRichard C Larock
Aug 20, 2009·Angewandte Chemie·Christopher S BryanMark Lautens
Jan 9, 2010·Journal of Combinatorial Chemistry·Chul-Hee ChoRichard C Larock
Feb 4, 2010·The Journal of Organic Chemistry·Saurabh Mehta, Richard C Larock
Jan 20, 2011·Journal of the American Chemical Society·Yifei LiQun Liu
Oct 9, 2012·Organic Letters·Durga Prasad HariBurkhard König
Oct 20, 2012·Chemical Society Reviews·Liandi WangZhengkun Yu
Nov 14, 2012·Chemical Society Reviews·Ling PanQun Liu
Apr 30, 2014·Organic Letters·Settu Muhamad RafiqArasambattu K Mohanakrishnan

❮ Previous
Next ❯

Citations

Jan 14, 2016·Chemical Reviews·Lin ZhangQun Liu
May 28, 2020·Chemical Society Reviews·Jiang LouZhengkun Yu

❮ 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.