Synthesis and Structural Elucidation of Novel Spiropyrazolines Precursors to Spiro-gem-dimethylcyclopropanes

2005 ◽  
Vol 2005 (8) ◽  
pp. 498-501
Author(s):  
Karim Ben Ali ◽  
Najeh Boukamcha ◽  
Abdelkader Khemiss ◽  
Marie-Thérèse Martin
Keyword(s):  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Structural Elucidation ◽  
Dipolar Cycloaddition

1,3-dipolar cycloaddition reaction of 2-diazopropane (DAP) 1 with 2-arylidene-1-tetralone 2a–b led exclusively to spiro-Δ1-pyrazolines 3a–b. When 4-methyl-2-arylidene-1-tetralones 2c–d was used as starting dipolarophile a mixture of diastereiosomeric cycloadducts 4a–b and 5a–b was obtained. The photochemical nitrogen-extrusion studied for spiropyrazolines 3a–b and 4a–b led stereospecifically to spiro-gem-dimethylcyclopropanes. In all cases, the reaction regiochemistry and stereochemistry was discussed on the basis of 2D-NMR experiments.

scholarly journals Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate

Molbank ◽  
10.3390/m1167 ◽  
2020 ◽  
Vol 2020 (4) ◽  
pp. M1167
Author(s):  
Serigne Abdou Khadir Fall ◽  
Saïd Achamlale ◽  
Younas Aouine ◽  
Asmae Nakkabi ◽  
Hassane Faraj ◽  
...  
Keyword(s):  
Infrared Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Solvent Mixture ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Sulfate Pentahydrate ◽  
Copper Sulfate Pentahydrate

The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out in a water/ethanol solvent mixture (50/50), in the presence of copper sulfate pentahydrate and catalytic sodium ascorbate. The characterization of the structure of the resulting 1,4-regioisomer was performed by 1D and 2D-NMR experiments, infrared spectroscopy, and elemental analysis.

scholarly journals Microwave-Assisted Regioselective Synthesis and 2D-NMR Studies of New 1,2,3-Triazole Compounds Derived from Acridone

2021 ◽  
Vol 2021 ◽  
pp. 1-10
Author(s):  
Mohammed Aarjane ◽  
Siham Slassi ◽  
Bouchra Tazi ◽  
Amina Amine
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Cycloaddition Reaction ◽  
Reaction Times ◽  
2D Nmr ◽  
Dipolar Cycloaddition ◽  
Microwave Assisted Synthesis ◽  
Nmr Studies ◽  
Microwave Assisted ◽  
Acridone Derivatives

A simple and mild protocol towards the synthesis of new 1,2,3-triazole compounds derived from acridone has been developed via regiospecific 1,3-dipolar cycloaddition reaction between 10-(prop-2-yn-1-yl)acridone derivatives and aromatic azides using CuI as a catalyst. The cycloaddition reaction has been performed using conventional as well as microwave-assisted methods. Microwave-assisted synthesis caused a significant reduction in the reaction times and improvement in the yields of all the synthesized compounds compared with the conventional method. The structure of the 1,4-disubstituted 1,2,3-triazoles has been elucidated by IR, HRMS, 1H-NMR, 13C-NMR, and 2D NMR (1H-13C HMBC, 1H-1H COSY, and 1H-1H NOESY) spectroscopies.

New Pyrrolo[1,2-b]pyridazine Derivatives by 1,3-Dipolar Cycloaddition of Mesoionic Oxazolopyridazinone

2008 ◽  
Vol 59 (11) ◽  
Author(s):  
Miron Teodor Caproiu ◽  
Florea Dumitrascu ◽  
Mino R. Caira
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridazine Derivatives ◽  
New Compounds

New pyrrolo[1,2-b]pyridazine derivatives 8a-f were synthesized by 1,3-dipolar cycloaddition reaction between mesoionic 1,3-oxazolo[3,2-b]pyridazinium-2-oxides and diethyl or diisopropyl acetylenedicarboxylate as alkyne dipolarophiles. The structures of the new compounds were assigned by elemental analysis and NMR spectroscopy.

Copper-catalyzed Convenient Synthesis and SAR Studies of Substituted-1,2,3-triazole as Antimicrobial Agents

2018 ◽  
Vol 16 (1) ◽  
pp. 3-10
Author(s):  
Aniket P. Sarkate ◽  
Kshipra S. Karnik ◽  
Pravin S. Wakte ◽  
Ajinkya P. Sarkate ◽  
Ashwini V. Izankar ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Triazole Derivatives ◽  
Sar Studies ◽  
Convenient Synthesis ◽  
Antibacterial And Antifungal

Background:A novel copper-catalyzed synthesis of substituted-1,2,3-triazole derivatives has been developed and performed by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The reaction is one-pot multicomponent.Objective:We state the advancement and execution of a methodology allowing for the synthesis of some new substituted 1,2,3-triazole analogues with antimicrobial activity.Methods:A series of triazole derivatives was synthesized by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, IR, MS and elemental analysis. All the synthesized compounds were tested for their antimicrobial activity against a series of strains of Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus nigar for antifungal activity, respectively.Results and Conclusion:From the antimicrobial data, it was observed that all the newly synthesized compounds showed good to moderate level of antibacterial and antifungal activity.

Rapid Access to Novel 1,2,3-Triazolo-Heterocyclic Scaffolds via Tandem Knoevenagel Condensation/Azide–Alkyne 1,3-Dipolar Cycloaddition Reaction in One Pot

2014 ◽  
Vol 16 (9) ◽  
pp. 466-477 ◽  
Author(s):  
Ram Awatar Maurya ◽  
Praveen Reddy Adiyala ◽  
D. Chandrasekhar ◽  
Chada Narsimha Reddy ◽  
Jeevak Sopanrao Kapure ◽  
...  
Keyword(s):  
Knoevenagel Condensation ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Rapid Access

Synthesis of novel isoxazole-benzoquinone hybrids via 1,3-dipolar cycloaddition reaction as key step

2012 ◽  
Vol 53 (32) ◽  
pp. 4108-4113 ◽  
Author(s):  
P. Ravi Kumar ◽  
Manoranjan Behera ◽  
K. Raghavulu ◽  
A. Jaya Shree ◽  
Satyanarayana Yennam
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition

Bifunctional AgOAc/ThioClickFerrophos catalyzed asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides to nitroalkenes

Tetrahedron ◽  
2016 ◽  
Vol 72 (21) ◽  
pp. 2666-2670 ◽  
Author(s):  
Midori Kimura ◽  
Yukiko Matsuda ◽  
Akihiro Koizumi ◽  
Chihiro Tokumitsu ◽  
Yuichiro Tokoro ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition
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