1,3-Dipolar cycloaddition reactions to the C:X-M fragment. 9. Synthesis and characterization of mononuclear imino ketone complexes Fe(CO)3(tert-BuN:CHCR:O) and their use in chemoselective cycloaddition reactions with dimethyl acetylenedicarboxylate resulting in the formation of Fe(CO)3(butenolide) complexes

1993 ◽  
Vol 12 (10) ◽  
pp. 4172-4181 ◽  
Author(s):  
Maarten van Wijnkoop ◽  
Ron Siebenlist ◽  
Paul P. M. de Lange ◽  
Hans Werner Fruhauf ◽  
Kees Vrieze ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Synthesis And Characterization ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate

Synthesis and characterization of new 1,4 and 1,5-disubstituted glucopyranosyl 1,2,3-triazole by 1,3-dipolar cycloaddition

2009 ◽  
Vol 929 (1-3) ◽  
pp. 6-9 ◽  
Author(s):  
Abdelkarim El Moncef ◽  
El Mestafa El Hadrami ◽  
Abdeslem Ben-Tama ◽  
Carmen Ramírez de Arellano ◽  
Elena Zaballos-Garcia ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Synthesis And Characterization

scholarly journals Huisgen [3 + 2] Dipolar Cycloadditions of Phthalazinium Ylides to Activated Symmetric and Non-Symmetric Alkynes

Molecules ◽  
2020 ◽  
Vol 25 (19) ◽  
pp. 4416
Author(s):  
Vasilichia Antoci ◽  
Costel Moldoveanu ◽  
Ramona Danac ◽  
Violeta Mangalagiu ◽  
Gheorghita Zbancioc
Keyword(s):  
Reaction Time ◽  
Comparative Study ◽  
Cycloaddition Reaction ◽  
Environmentally Friendly ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Thermal Heating ◽  
Dipolar Cycloadditions ◽  
Methyl Propiolate

We present herein a straightforward and efficient pathway for the synthesis of pyrrolophthalazine cycloadducts via Huisgen [3 + 2] dipolar cycloaddition reactions of phthalazinium ylides to methyl propiolate or dimethyl acetylenedicarboxylate (DMAD). A thoroughly comparative study concerning the efficiency of synthesis, conventional thermal heating (TH) versus microwave (MW) and ultrasound (US) irradiation, has been performed. The cycloaddition reactions of phthalazinium ylides to methyl propiolate occur regiospecific, with a single regioisomer being obtained. Under conventional TH, the cycloaddition reaction of phthalazinium ylides with DMAD occurs to a mixture of inseparable partial and fully aromatized pyrrolophthalazine cycloadducts, while MW or US irradiation are leading only to fully aromatized compounds, with the reactions becoming selective. A feasible mechanism for formation of fully aromatized compounds is presented. Besides selectivity, it has to be noticed that the reaction setup under MW or US irradiation offer a number of other certain advantages: higher yields, decreasing of the amount of used solvent comparative with TH, decreasing of the reaction time from hours to minutes and decreasing of the consumed energy; consequently, these reactions could be considered environmentally friendly.

Environmentally benign synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates using CeO2 nanoparticles as a reusable and robust catalyst

2016 ◽  
Vol 71 (11) ◽  
pp. 1135-1140 ◽  
Author(s):  
Javad Safaei-Ghomi ◽  
Mehrnoosh Asgari-Kheirabadi ◽  
Hossein Shahbazi-Alavi
Keyword(s):  
Condensation Reaction ◽  
Ceo2 Nanoparticles ◽  
Environmentally Benign ◽  
High Yield ◽  
Synthesis And Characterization ◽  
Dimethyl Acetylenedicarboxylate ◽  
One Pot ◽  
Efficient Catalyst ◽  
Benign Synthesis

AbstractIn this work, we report the synthesis and characterization of CeO2 nanoparticles as an efficient catalyst for the preparation of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates via one-pot four-component condensation reaction of dimethyl acetylenedicarboxylate, hydrazine hydrate, malononitrile, and aldehydes in aqueous medium. The use of a non-hazardous organic solvent, easy recovery of the catalyst, compatibility with various functional groups, and high yield of the products make the protocol attractive, greener, and economic.

SYNTHESIS AND CHARACTERIZATION OF TRIAZOLE CONTAINING LIQUID CRYSTALLINE POLYMERS THROUGH 1,3-DIPOLAR CYCLOADDITION POLYMERIZATION

2009 ◽  
Vol 27 (06) ◽  
pp. 761 ◽  
Author(s):  
Devamani Srividhya ◽  
Sundaram Manjunathan ◽  
Sivashankaran Nithyanandan ◽  
Subramanan Balamurugan ◽  
Sengodan Senthil
Keyword(s):  
Liquid Crystalline ◽  
Liquid Crystalline Polymers ◽  
Dipolar Cycloaddition ◽  
Synthesis And Characterization ◽  
Crystalline Polymers

Synthesis and Characterization of Reactive Energetic Plasticizers for Poly(glycidyl azide-co-tetramethylene glycol)-Based Polyurethane Binders

2021 ◽  
Vol 21 (7) ◽  
pp. 4110-4115
Author(s):  
Yechen Shen ◽  
Younghwan Kwon
Keyword(s):  
Click Reaction ◽  
Point Of View ◽  
Dipolar Cycloaddition ◽  
Synthesis And Characterization ◽  
Catalyst Free ◽  
Energetic Plasticizers ◽  
Glycidyl Azide

Two reactive energetic plasticizers, 3-((2,2-dinitropropoxy)methoxy)prop-1-yne and 4-((2,2-dinitropropoxy)methoxy)but-1-yne which can react with an azido-containing poly(glycidyl azide-co-tetramethylene glycol) prepolymer by cupper-free 1,3-dipolor cycloaddition (“Click”) reaction, were synthesized and characterized, in order to investigate their plasticizing performance and catalyst-free 1,3-dipolar cycloaddition reactivity on energetic polyurethane binders. Two reactive energetic plasticizers showed better plasticizing performance than commercial energetic plasticizers. In the reactivity point of view, 3-((2,2-dinitropropoxy)methoxy)prop-1-yne exhibited higher Click reactivity than 4-((2,2-dinitropropoxy)methoxy)but-1-yne. Two synthesized plasticizers were found to fulfill the requirements for use as reactive energetic plasticizers.

scholarly journals Synthesis and Characterization of Some New Nucleoside Analogues from Substituted Benzimidazole via 1,3-Dipolar cycloaddition

2016 ◽  
Vol 13 (2) ◽  
pp. 298-306
Author(s):  
Baghdad Science Journal
Keyword(s):  
Benzoic Acid ◽  
Benzimidazole Derivative ◽  
Cycloaddition Reaction ◽  
Nucleoside Analogues ◽  
Dipolar Cycloaddition ◽  
Synthesis And Characterization ◽  
Propargyl Bromide ◽  
Sugar Moiety ◽  
Ft Ir

This paper includes the synthesis of some new nucleoside analogues starting with 2-substituted benzimidazole derivative (7-9), that synthesized by condensation of O-phenylenediamine with p-chloro benzaldehyde and two substituted benzoic acid , which on nucleophilic substitution with propargyl bromide gave a new N-substituted compounds (10-12). D-Fructose and D-galactose were chosen as a sugar moiety which were protected, brominated and azotated to give azido sugars (5) and (6), then they were subjected to 1,3-dipolar cycloaddition reaction with N-substuted compounds afforded bloked nucleoside analoges (13-16), which after hydrolysis gave our target the free nucleoside analogues (17-20). All prepared compounds were identified by FT-IR and some of them with 1H-NMR and 13C-NMR.

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