scholarly journals Synthesis of Novel N-Heterocyclic Compounds Containing 1,2,3-Triazole Ring System via Domino, “Click” and RDA Reactions

Molecules ◽  
2019 ◽  
Vol 24 (4) ◽  
pp. 772 ◽  
Author(s):  
Márta Palkó ◽  
Mohamed El Haimer ◽  
Zsanett Kormányos ◽  
Ferenc Fülöp
Keyword(s):  
Heterocyclic Compounds ◽  
Click Reaction ◽  
Triazole Ring ◽  
Heterocyclic Ring ◽  
Ring System ◽  
Diels Alder ◽  
Ring Closure ◽  
Synthetic Route ◽  
13C Nuclear Magnetic Resonance ◽  
Nmr Methods

An uncomplicated, high-yielding synthetic route has been developed to constitute complicated heterocycles, applying domino, click and retro-Diels–Alder (RDA) reaction sequences. Starting from 2-aminocarboxamides, a new set of isoindolo[2,1-a]quinazolinones was synthesized with domino ring closure. A click reaction was performed to create the 1,2,3-triazole heterocyclic ring, followed by an RDA reaction resulting in dihydropyrimido[2,1-a]isoindole-2,6-diones. The absolute configuration, concluded by the norbornene structure that served as a chiral source, remained constant throughout the transformations. The structure of the synthesized compounds was examined by 1H and 13C Nuclear Magnetic Resonance (NMR) methods.

Organophosphorus compounds. XX. Approaches to the synthesis of 2,3-Dihydro-1H-1,2-benzazaphospholes involving C-C and C-P ring closure

1984 ◽  
Vol 37 (5) ◽  
pp. 1009 ◽  
Author(s):  
DJ Collins ◽  
PF Drygala ◽  
JM Swan
Keyword(s):  
Organophosphorus Compounds ◽  
Heterocyclic Ring ◽  
Ring System ◽  
Ring Closure ◽  
Aluminium Chloride

Reaction of chloromethylphosphonic dichloride (9) with N-methylaniline gave N,N'-dimethyl-N,N'-diphenylchloromethylphosphonodiarnide (10) which upon treatment with aluminium chloride underwent intramolecular Friedel-Crafts alkylation to afford 1-methyl-2-(N'-methyl-N'-phenylamino)-2,3-dihydro-1N-l,2-benzazaphosphole 2-oxide(13a). Similarly, N-methyl-N-phenyl(ch1oromethy1)phenylphosphinamide (15) was cyclized to give 1-methyl-2-phenyl-2,3-dihydro-1H-1,2-benzazaphosphole2-oxide (1 3b). Some unsuccessful approaches to this heterocyclic ring system are also reported.

A Facile Total Synthesis of Mubritinib

Synthesis ◽  
2021 ◽  
Vol 53 (05) ◽  
pp. 978-982
Author(s):  
Chunxiang Kuang ◽  
Rong Wang ◽  
Menghan Cui ◽  
Qing Yang
Keyword(s):  
Total Synthesis ◽  
Click Reaction ◽  
Triazole Ring ◽  
Ring System ◽  
Industrial Scale ◽  
Key Steps ◽  
The Way

AbstractA five-step, practical, and concise total synthesis of mubritinib is described. The synthesis utilized Friedel–Crafts acylation, click reaction, reduction, and demethylation for the construction of the triazole ring system as key steps. Another important feature of this synthesis is the Bredereck oxazole synthesis. The main advantages of this process are the improved yield and decreased number of reaction steps, which paves the way for the industrial-scale synthesis of mubritinib.

Total Synthesis of (±)-Illisimonin A, a Neuroprotective Sesquiterpenoid from the Fruits of Illicium simonsii

2019 ◽  
Author(s):  
Alexander S. Burns ◽  
Scott Rychnovsky
Keyword(s):  
Total Synthesis ◽  
Cell Injury ◽  
Glucose Deprivation ◽  
Ring System ◽  
Diels Alder ◽  
Synthetic Route ◽  
Neuroprotective Effects ◽  
Carbon Framework ◽  
Highly Strained ◽  
Type 3

<p>Illisimonin A was isolated from Illicium simonsii and has a previously unreported tricyclic carbon framework. It displayed neuroprotective effects against oxygen-glucose deprivation-induced cell injury in SH-SY5Y cells. It incorporates a highly strained trans-pentalene ring system. We report the first synthesis of illisimonin A. Notable steps in the route include a 1,3-dioxa-2-silacyclohexenetemplated Diels-Alder cycloaddition and type-3 semipinacol rearrangement to generate the trans-pentalene. The final step is an iron-catalyzed C-H oxidation. The synthetic route is robust, with 94 mg prepared in a single pass.</p>

Total Synthesis of (±)-Illisimonin A, a Neuroprotective Sesquiterpenoid from the Fruits of Illicium simonsii

2019 ◽  
Author(s):  
Alexander S. Burns ◽  
Scott Rychnovsky
Keyword(s):  
Total Synthesis ◽  
Cell Injury ◽  
Glucose Deprivation ◽  
Ring System ◽  
Diels Alder ◽  
Synthetic Route ◽  
Neuroprotective Effects ◽  
Carbon Framework ◽  
Highly Strained ◽  
Type 3

<p>Illisimonin A was isolated from Illicium simonsii and has a previously unreported tricyclic carbon framework. It displayed neuroprotective effects against oxygen-glucose deprivation-induced cell injury in SH-SY5Y cells. It incorporates a highly strained trans-pentalene ring system. We report the first synthesis of illisimonin A. Notable steps in the route include a 1,3-dioxa-2-silacyclohexenetemplated Diels-Alder cycloaddition and type-3 semipinacol rearrangement to generate the trans-pentalene. The final step is an iron-catalyzed C-H oxidation. The synthetic route is robust, with 94 mg prepared in a single pass.</p>

scholarly journals Synthesis of heterocyclic ring (1,2,4-triazole) as polystyrene photo stabilizer

2021 ◽  
Vol 9 (2) ◽  
pp. 051-057
Author(s):  
Shahad Muhammad ◽  
Ahmed Ahmed
Keyword(s):  
Heterocyclic Compounds ◽  
Uv Light ◽  
Alkyl Halide ◽  
Benzyl Bromide ◽  
Triazole Ring ◽  
Heterocyclic Ring ◽  
Uv Absorber ◽  
Schiff Base Compound ◽  
Instrumental Methods ◽  
Base Compound

New heterocyclic compounds contain triazole ring (play very important role in photostabilization as UV absorber) synthesized by reaction between the di Schiff base (compound 3) with aromatic alkyl halide (Benzyl bromide) and shows there activity as photostabilizer for polystyrene through exposure to the UV-Light (300 hours). Finally Infrared spectroscopy, 1H-NMR, 13C-NMR and instrumental methods were used to characterize products and their structures.

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