Design of pyrazolo-pyrrolo-pyrazines and pyrazolo-pyrrolo-diazepines via AuCl₃-catalyzed and NaH-supported cyclization of N-propargyl pyrazoles

The Journal of Organic Chemistry
Sinan Basceken, Metin Balci

Abstract

A concise synthetic methodology for new heterocyclic scaffolds, such as pyrazolo-pyrrolo-pyrazine and pyrazolo-pyrrolo-diazepine skeletons, was developed. The key features of this method include (i) synthesis of pyrrole-derived α,β-alkynyl ketones, (ii) introduction of various substituents into the alkyne functionality by Sonogashira cross-coupling, (iii) synthesis of pyrazole units by the reaction of α,β-alkynyl compounds with hydrazine monohydrate, (iv) gold-catalyzed cyclization of pyrazoles with alkyne units, and (v) cyclization with NaH. Furthermore, this methodology allows various substituents to be introduced into all positions of the target compounds.

References

Feb 20, 2007·Chemical Reviews·Rafael Chinchilla, Carmen Najera
Jun 22, 2007·Chemical Reviews·A Stephen K Hashmi
Feb 19, 2008·The Journal of Organic Chemistry·Xiaohu Deng, Neelakandha S Mani
Mar 25, 2008·Journal of the American Chemical Society·Natalia Chernyak, Vladimir Gevorgyan
Jun 8, 2011·Beilstein Journal of Organic Chemistry·Benito Alcaide, Pedro Almendros
Jun 23, 2011·Organic Letters·Buddhadeb Chattopadhyay, Vladimir Gevorgyan
Jul 12, 2011·The Journal of Organic Chemistry·Metin ZoraCeyda Yazici
Aug 25, 2011·Chemical Reviews·Kerry Gilmore, Igor V Alabugin
Oct 1, 2011·Angewandte Chemie·Gábor KovácsGregori Ujaque
Sep 25, 2012·The Journal of Organic Chemistry·Niranjan Panda, Ashis Kumar Jena
May 2, 2013·Organic & Biomolecular Chemistry·Nicolai I NikishkinWillem Verboom
May 8, 2013·The Journal of Organic Chemistry·Nurettin MengesMetin Balci
Jun 15, 2013·Beilstein Journal of Organic Chemistry·Benito AlcaideIsrael Fernández
Jul 3, 2013·Journal of Enzyme Inhibition and Medicinal Chemistry·Jimi Marin Alex, Raj Kumar
Aug 6, 2013·Organic Letters·Colombe GronnierFabien Gagosz
Oct 9, 2013·European Journal of Medicinal Chemistry·Vinod KumarAnil Kumar Sharma
Oct 10, 2013·Angewandte Chemie·Rachel E M Brooner, Ross A Widenhoefer
Jan 17, 2014·Accounts of Chemical Research·Benito Alcaide, Pedro Almendros
Apr 5, 2014·The Journal of Organic Chemistry·Thomas KlattPaul Knochel

❮ Previous
Next ❯

Citations

Sep 24, 2015·Chemistry : a European Journal·Karel ŠkochPetr Štěpnička
Aug 19, 2015·Organic & Biomolecular Chemistry·Stefan AichhornWolfgang Schöfberger
May 21, 2015·Organic Letters·Sinem GuvenMetin Balci
Jan 29, 2020·Chemistry : a European Journal·Jose S S Neto, Gilson Zeni
Mar 3, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Mandeep Kaur HunjanJoydev K Laha
Jun 2, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Chandrasekar Praveen
Jul 24, 2021·Journal of Inorganic Biochemistry·Guillermo CarroneFabio Doctorovich

❮ 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.