ChemInform Abstract: Amidine‐Enediamine Tautomerism: Addition of Isocyanates to 2‐ Substituted 1H‐Perimidines. Some Syntheses under Microwave Irradiation.

Cado, F.; DiMartino, Joseph.; Jacquault, P.; Bazureau, Jean Pierre; Hamelin, J.

doi:10.1002/chin.199651139

Cited by 3 publications

(3 citation statements)

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“…Further evidence for the assigned structure 8 is provided by its mass spectrum, which revealed ion peaks at m/z 168 and 121, corresponding to the perimidine and HO-C 6 H 4 -CO fragments, respectively. This assignment is in good agreement with literature data indicating the stability of perimidines to be greater than that of diazocines [37,38,39].…”

Section: Resultssupporting

confidence: 92%

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

et al. 2014

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Two series of naphtho[1,8-ef][1,4]diazepines and pyrrolo[1,2-a]perimidines were prepared starting from 1,8-diaminonaphthalene and hydrazonoyl chlorides. The structures of the products were determined on the basis of their spectral data and elemental analyses. The mechanism of formation of such products was also discussed. The prepared compounds were screened for their antitumor activity against three cell lines, namely, MCF-7, TK-10 and UACC-62, and some derivatives showed promising activity.

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Section: Resultssupporting

confidence: 92%

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

et al. 2014

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“…Furthermore, the phenyl hydrazone derivative 68a undergoes cyclization via methyl alcohol elimination under MWI catalysis, resulting in the formation of N-phenylpyridazine 69a. Interesting chemical transformations (Figure 12) are presented in publication [62], which explores solvent-free and pipyridine-catalyzed reactions under microwave irradiation (MWI), an effective method for dry organic syntheses [63][64][65][66][67][68][69][70][71][72]. Phenylhydrazone (HGa) and dimethylhydrazone (HGb) react with acetoacetic ether in a 1:1 ratio to form conjugated compounds 68a and 68b.…”

Section: Reagentsmentioning

confidence: 99%

The Recycling of Substandard Rocket Fuel N,N-Dimethylhydrazine via the Involvement of Its Hydrazones Derived from Glyoxal, Acrolein, Metacrolein, Crotonaldehyde, and Formaldehyde in Organic Synthesis

Ivanova,

Osipova,

Vasilieva

et al. 2023

IJMS

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“Heptil” (unsymmetrical dimethylhydrazine—UDMH) is extensively employed worldwide as a propellant for rocket engines. However, UDMH constantly loses its properties as a result of its continuous and uncontrolled absorption of moisture, which cannot be rectified. This situation threatens its long-term usability. UDMH is an exceedingly toxic compound (Hazard Class 1), which complicates its transportation and disposal. Incineration is currently the only method used for its disposal, but this process generates oxidation by-products that are even more toxic than the original UDMH. A more benign approach involves its immediate reaction with a formalin solution to form 1,1–dimethyl-2-methylene hydrazone (MDH), which is significantly less toxic by an order of magnitude. MDH can then be polymerized under acidic conditions, and the resulting product can be burned, yielding substantial amounts of nitrogen oxides. This review seeks to shift the focus of MDH from incineration towards its application in the synthesis of relatively non-toxic and readily available analogs of various pharmaceutical substances. We aim to bring the attention of the international chemical community to the distinctive properties of MDH, as well as other hydrazones (such as glyoxal, acrolein, crotonal, and meta-crolyl), wherein each structural fragment can initiate unique transformations that have potential applications in molecular design, pharmaceutical research, and medicinal chemistry.

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“…New heterocyclic ketene aminals have been obtained in yields ranging from 60 to 94 % [89] starting from ethyl 1H-perimidine-2-acetate or acetonitrile and isocyanates (Scheme 8.63).…”

Section: Addition Of Isocyanates To 2-substituted 1h-perimidinementioning

confidence: 99%

Microwaves in Heterocyclic Chemistry

Hamelin

Bazureau

Texier‐Boullet

2002

Microwaves in Organic Synthesis

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The palladium-catalyzed Heck [1], Suzuki [2] and Stille [3] reactions are robust and general methods for C±C bond-formation and have therefore emerged as important reactions in the synthesis of natural heterocyclic compounds.Hallberg and coworkers [4 a] have used a single-mode microwave oven [4 b] at 50 W to improve radical-mediated reduction and cyclization of the heterohalide 1 with HSn(CH 2 CH 2 C 10 F 21 ) 3 2 in benzotrifluoride (BTF). The authors claim the preparation of 3 in high yield (93 %) after 5 min, as illustrated in Scheme 8.1.The efficiency of fluorous Stille coupling reactions [5 a] is enhanced by use of microwave irradiation (Scheme 8.2). The reaction proceeds in 79 % yield after 2 min with DMF as the microwave-active solvent.

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ChemInform Abstract: Amidine‐Enediamine Tautomerism: Addition of Isocyanates to 2‐ Substituted 1H‐Perimidines. Some Syntheses under Microwave Irradiation.

Cited by 3 publications

References 0 publications

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

The Recycling of Substandard Rocket Fuel N,N-Dimethylhydrazine via the Involvement of Its Hydrazones Derived from Glyoxal, Acrolein, Metacrolein, Crotonaldehyde, and Formaldehyde in Organic Synthesis

Microwaves in Heterocyclic Chemistry

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