3-Arylaziridine-2-carboxylic Acid Derivatives and (3-Arylaziridin-2-yl)ketones: The Aziridination Approaches DOI Open Access

Boriss Štrumfs,

Romans Uljanovs, Kirils Velikijs

et al.

International Journal of Molecular Sciences, Journal Year: 2021, Volume and Issue: 22(18), P. 9861 - 9861

Published: Sept. 13, 2021

Aziridination reactions represent a powerful tool in aziridine synthesis. Significant progress has been achieved this field the last decades, whereas highly functionalized aziridines including 3-arylated aziridine-2-carbonyl compounds play an important role both medical and synthetic chemistry. For reasons listed, current review we have focused on ways to obtain recent advances (mainly since year 2000) methodology of synthesis these via aziridination.

Language: Английский

Stereoselective synthesis and applications of spirocyclic oxindoles DOI Creative Commons
Alexander J. Boddy, James A. Bull

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(5), P. 1026 - 1084

Published: Jan. 1, 2021

This review summaries recent synthetic developments towards spirocyclic oxindoles and applications as valuable medicinal targets.

Language: Английский

Citations

255

Syntheses and reactivity of spiro-epoxy/aziridine oxindole cores: developments in the past decade DOI
Akash P. Sakla,

Pritish Kansal,

Nagula Shankaraiah

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(42), P. 8572 - 8596

Published: Jan. 1, 2020

Spiro-epoxy/aziridine oxindole frameworks are considered as an efficient structural toolbox to obtain C3-functionalised derivatives. These 3,3'-spiro-cyclic precursors highly susceptible towards nucleophiles owing their inherent ring strain. Their versatile reactivity has opened many potential synthetic transformations, allowing access bioactive molecules well natural products. The present review aims elaborate various enabling strategies applied in the successful synthesis of strained spiro-cyclic scaffolds. Furthermore, nucleophilic ring-opening/expansion and cycloaddition reactions spiro-epoxy/aziridine discussed. Moreover, mechanistic insights define regio- stereo-chemical outcome products have also been highlighted briefly.

Language: Английский

Citations

36

Spiro-Heterocycles: Recent Advances in Biological Applications and Synthetic Strategies DOI

D Basavaraja,

Sameer Kumar Devarakonda, A. S.

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134468 - 134468

Published: Jan. 1, 2025

Language: Английский

Citations

0

Novel and convenient one-pot strategy for regioselective synthesis of new 5-aryl-3-methyl-1-phenyl-1,2-dihydro-7aH-pyrazolo[3,4-c]pyridazin-7a-ol derivatives DOI
Mehdi Rimaz, Hossein Mousavi,

Laya Nikpey

et al.

Research on Chemical Intermediates, Journal Year: 2017, Volume and Issue: 43(7), P. 3925 - 3937

Published: Jan. 6, 2017

Language: Английский

Citations

25

Green chemistry oriented multi-component strategy to hybrid heterocycles DOI

Balakrishnan Rajarathinam,

Kandhasamy Kumaravel,

G. Vasuki

et al.

RSC Advances, Journal Year: 2016, Volume and Issue: 6(77), P. 73848 - 73852

Published: Jan. 1, 2016

An oxindole decorated 4H-chromene scaffold has been synthesized in water under catalyst-free reaction conditions at ambient temperature by integrating the guiding principles of Diversity Oriented Synthesis (DOS) and green chemistry.

Language: Английский

Citations

24

Iodide-Mediated Synthesis of Spirooxindolo Dihydrofurans from Iodonium Ylides and 3-Alkylidene-2-oxindoles DOI

Benjamin A. Laevens,

Jason Tao, Graham K. Murphy

et al.

The Journal of Organic Chemistry, Journal Year: 2017, Volume and Issue: 82(22), P. 11903 - 11908

Published: July 27, 2017

An iodide-mediated reaction between cyclic iodonium ylides of 1,3-dicarbonyls and 3-alkylidene-2-oxindoles results in 3H-spiro[furan-2,3′-indolin]-2′-ones. The was tolerant to substitutions on both the alkylidene ylide substrates provided access 19 new, densely functionalized polycyclic spirocycles typically high yield.

Language: Английский

Citations

21

Base-catalyzed one-pot synthesis of dispiro-1,3-dioxolane bisoxindoles from N-methylisatin and methyl propiolate DOI
Su Yeon Kim,

Hwa Jung Roh,

Da Young Seo

et al.

Tetrahedron Letters, Journal Year: 2017, Volume and Issue: 58(10), P. 914 - 918

Published: Jan. 19, 2017

Language: Английский

Citations

19

I2/TBHP mediated diastereoselective synthesis of spiroaziridines DOI

K. T. Ashitha,

Puthiya Purayil Vinaya,

A. Siva Krishna

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(8), P. 1588 - 1593

Published: Jan. 1, 2020

A simple metal free protocol for the diastereoselective synthesis of spiroaziridines using easily accessible substrates is disclosed.

Language: Английский

Citations

17

Intramolecular Imino-ene Reaction of 2H-azirines with Alkenes: Rapid Construction of Spiro NH Aziridines from Vinyl Azides DOI

Tai-Shang Liu,

Hao Zhou,

Peng Chen

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(11), P. 3156 - 3160

Published: May 16, 2018

A range of novel (poly)cyclic alkaloids incorporating an unprecedented 1,5-diazaspiro[2.4]heptane core that carry a spiro NH aziridine moiety and 7-vinyl group are constructed from the thermal reaction vinyl azides with tethered alkenes. Vinyl converted to 2H-azirines in situ, which serve as enophiles for intramolecular imino-ene reactions suitable High stereoselectivity specificity have been achieved this azirines.

Language: Английский

Citations

17

One-pot pseudo three-component condensation reaction of arylglyoxal monohydrates with 1-ethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione for the synthesis of new pyrano[2,3-d:6,5-d’]dipyrimidines as HIV integrase inhibitor-like frameworks using two different environmentally benign catalytic systems DOI
Mehdi Rimaz, Hossein Mousavi, Behzad Khalili

et al.

Journal of the Iranian Chemical Society, Journal Year: 2019, Volume and Issue: 16(8), P. 1687 - 1701

Published: March 11, 2019

Language: Английский

Citations

16