Generation and dienophilic properties of 1‐benzyl‐1<i>H</i>‐1,2,3‐triazolo[4,5‐<i>d</i>]pyridazine‐4,7‐dione

Theocharis, A.; Alexandrou, Nicholas; Terzis, Aris

doi:10.1002/jhet.5570270643

Cited by 19 publications

(8 citation statements)

References 17 publications

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“…Calcd for C 22 H 16 N 6 O: C,69.46;H,4.24;N,22.09. Found C,69.50;H,4.32;N,22.21. General procedure for the reaction of benzotriazolylcarbonyltriazole 20 with amines A solution of 1H-1,2,3-benzotriazol-1-yl(1-benzyl-5-phenyl-1H-1,2,3-triazol-4-yl)methanone (20) (0.38 g, 1 mmol) with an appropriate amine (1 mmol) in CH 2 Cl 2 (5 mL) was stirred at 25 o C for 12…”

Section: General Procedures For Triazole Formation Under Microwave Irrmentioning

confidence: 99%

1,3-Dipolar cycloadditions of organic azides to ester or benzotriazolylcarbonyl activated acetylenic amides

Katritzky¹,

Zhang²,

Singh³

et al. 2003

Arkivoc

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Reactions of 3-lithiopropiolate 10 with isocyanates or diisocyanates gave monocarbamoylpropiolates 11a,b and bis-carbamoylpropiolates 12a−d, in 40−76% yields. 1,3-Dipolar cycloadditions of benzyl azide (1a) and mono-acetylenes 11a,b under thermal conditions gave mono-triazoles 13a,b in 83 and 84% yields, respectively. The structure of 13a was confirmed by Xray crystallography. Microwave induced cycloadditions of mono-azide 1a with biscarbamoylpropiolates 12a−d furnished the bis-triazoles 14a−d. Similar reactions of 3-(azidomethyl)-3-methyloxetane (15) with mono-acetylenes 11a,b or bis-acetylenes 12a,d produced the mono-and bis-triazoles 16a,b and 17a,b, respectively. Reactions of 1,4-bis(azidomethyl)benzene (1b) with mono-acetylenes 11a,b gave the azido-triazoles 18a,b and microwave irradiation with simultaneous air-cooling gave bis-triazoles 19a,b. 1,3-Dipolar cycloaddition of benzotriazolylcarbonyl-substituted acetylene 4 and benzyl azide (1a) proceeded smoothly under microwave irradiation or thermal conditions to give the corresponding triazole 20, which on further treatment with a variety of amines gave the C-carbamoyl triazoles 21a−d in 54−91% yields.

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Section: General Procedures For Triazole Formation Under Microwave Irrmentioning

confidence: 99%

1,3-Dipolar cycloadditions of organic azides to ester or benzotriazolylcarbonyl activated acetylenic amides

Katritzky¹,

Zhang²,

Singh³

et al. 2003

Arkivoc

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“…Reactions of benzyl chloride, γ -phenylpropyl chloride, or α , α ‘ -dichloro- p -xylene with sodium azide in ethanol/water (4:1) at reflux gave the corresponding azides 1 , 2 , or 6 in 85−97% yields 1-Piperidino-2-propyn-1-one ( 5 ) was similarly prepared from propiolic acid and piperidine in 68% yield.…”

mentioning

confidence: 99%

Synthesis of C-Carbamoyl-1,2,3-triazoles by Microwave-Induced 1,3-Dipolar Cycloaddition of Organic Azides to Acetylenic Amides

Katritzky

Singh

2002

J. Org. Chem.

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“…The syntheses of 1,4‐bis(azidomethyl)benzene ( p ‐BAB) and 1,3‐bis(azidomethyl)benzene( m ‐BAB) have been previously described in the literature . In order to synthesize these two diazide monomers, 700 mL of acetonitrile, α,α′‐dichloro‐ p ‐xylene (20.0 g, 0.114 mol) or α,α′‐dichloro‐ m ‐xylene (20.0 g, 0.114 mol), and sodium azide (29.64 g, 0.456 mol) were reacted together in a two‐necked flask at 78 °C for 48 h. After completion of the reaction, the mixture was cooled to room temperature, filtered to remove the generated NaCl, and extracted with distilled water and dichloromethane using a separating funnel for five times.…”

Section: Methodsmentioning

confidence: 99%

Epoxy resins toughened with in situ azide–alkyne polymerized polysulfones

Ying

Yang

Moon

et al. 2017

J of Applied Polymer Sci

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To simultaneously improve the fracture toughness and heat resistance of a cured toughened epoxy resin along with a reduction in its viscosity during the mixing process, two novel polysulfone‐type polymers are synthesized via azide–alkyne polymerization for use as toughening agents. The epoxy resin toughened with these polymers by in situ azide–alkyne polymerization during the cure process, which shows excellent processibility and based on the significantly lower viscosity (61 and 62 cP) during epoxy mixing process than that of commonly commercial polyethersulfone (PES, 127,612 cP). The novel polysulfone‐type polymer toughened epoxy resin showed the advantage in excellent fracture toughness than the PES toughened epoxy. In addition, the glass transition temperature of the novel polysulfone‐type polymer toughened epoxy resin is similar to that of the neat one (∼230 °C) and does not decrease, which implies excellent heat resistance of the toughened epoxy. These phenomena can be attributed to the formation of semi‐interpenetrating polymer networks comprising the epoxy network and the linear polysulfone‐type polymers. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 45790.

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Generation and dienophilic properties of 1‐benzyl‐1H‐1,2,3‐triazolo[4,5‐d]pyridazine‐4,7‐dione

Cited by 19 publications

References 17 publications

1,3-Dipolar cycloadditions of organic azides to ester or benzotriazolylcarbonyl activated acetylenic amides

1,3-Dipolar cycloadditions of organic azides to ester or benzotriazolylcarbonyl activated acetylenic amides

Synthesis of C-Carbamoyl-1,2,3-triazoles by Microwave-Induced 1,3-Dipolar Cycloaddition of Organic Azides to Acetylenic Amides

Epoxy resins toughened with in situ azide–alkyne polymerized polysulfones

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