Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences

The Journal of Organic Chemistry
Benito AlcaideRaquel Rodríguez-Acebes

Abstract

A novel approach to diversely functionalized spirocyclic oxindoles has been developed by using different metal-mediated carbonyl-addition/cyclization reaction sequences. Spirocyclization precursors, 2-indolinone-tethered homoallylic alcohols, (buta-1,3-dien-2-yl)methanols, and alpha-allenols have been obtained by regioselective addition of stabilized organoindium reagents to isatins in aqueous environment. Ruthenium-, silver-, and palladium-catalyzed reactions of the above unsaturated alcohol derivatives provided oxaspiro oxindoles.

References

Feb 19, 2003·Accounts of Chemical Research·Robert M Williams, Rhona J Cox
May 13, 2004·Chemical Reviews·Alexander Deiters, Stephen F Martin
Jun 17, 2004·Journal of the American Chemical Society·Soon Hyeok HongRobert H Grubbs
Aug 17, 2004·The Journal of Organic Chemistry·Sengodagounder MuthusamyMunirathinam Nethaji
Dec 21, 2004·Organic Letters·Yan ZhangJian-Hua Xu
Jul 21, 2005·Journal of the American Chemical Society·Ke DingShaomeng Wang

❮ Previous
Next ❯

Citations

Nov 1, 2012·Chemical Reviews·Zhi-Liang ShenTeck-Peng Loh
Sep 7, 2012·Chemical Reviews·Girija S Singh, Zelalem Y Desta
Sep 29, 2015·The Journal of Organic Chemistry·Eunhye LeeChan-Mo Yu
Jul 28, 2017·The Journal of Organic Chemistry·Benjamin A LaevensGraham K Murphy
Dec 6, 2014·Angewandte Chemie·Stefan A RuiderErick M Carreira
Jan 30, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Aliasghar Jarrahpour, Edris Ebrahimi
Aug 1, 2007·Angewandte Chemie·Benito AlcaideTeresa Martínez del Campo
Oct 24, 2007·Chemistry : a European Journal·Benito AlcaideMaría C Redondo
Jan 10, 2009·Chemistry : a European Journal·Benito AlcaideJosé L Marco-Contelles
Jul 11, 2009·Organic & Biomolecular Chemistry·Matthew Brichacek, Jón T Njardarson
Jun 8, 2012·Chemistry, an Asian Journal·Nitin T Patil
Mar 29, 2014·Chemical Society Reviews·María Paz Muñoz
Oct 1, 2015·Molecular Diversity·Tetyana L PavlovskaDmytro V Atamanuk
Feb 7, 2014·Chemical Society Reviews·Jean Le Bras, Jacques Muzart
Jun 11, 2014·Organic & Biomolecular Chemistry·Long ChenJian Zhou
Jun 27, 2019·Organic & Biomolecular Chemistry·Megha BalhaSubhas Chandra Pan
Feb 23, 2020·Organic & Biomolecular Chemistry·Prakash K WarghudeRamakrishna G Bhat
Sep 2, 2009·Organic Letters·M Paola CastaldiJohn A Porco
Nov 2, 2007·Chemical Reviews·Egle M BeccalliSilvia Sottocornola
May 20, 2011·Organic Letters·Jingqi WangKarl A Scheidt
Jul 4, 2012·Journal of the American Chemical Society·Dixit ParmarDavid J Procter
Dec 4, 2019·The Journal of Organic Chemistry·Jothi Lakshmi Nallasivam, Tushar Kanti Chakraborty
Aug 6, 2014·The Journal of Organic Chemistry·Toshiki NakanoAkio Kamimura

❮ Previous
Next ❯

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.