One-pot synthesis of [4-(tert-butyl)-1H-pyrrol-3-yl](phenyl)methanone from tosylmethyl isocyanide and carbonyl compound

Kaur, Ramandeep; Kumar, Kapil

doi:10.1007/s10593-018-2335-6

Cited by 14 publications

(4 citation statements)

References 23 publications

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“…1,2,4‐triazole containing molecules played an important role in biological and pharmacological activities. Based on our interest on organic and medicinal chemistry, [86–115] we summarized 1,2,4‐triazoles fused with various other heterocyclic molecules such as pyrimidine, pyridine, piperidine, indole, 1,2,3‐triazole etc. as anticancer agents.…”

Section: Discussionmentioning

confidence: 99%

Synthetic and Medicinal Perspective of 1,2,4‐Triazole as Anticancer Agents

Rathod

Kumar

2022

Chemistry & Biodiversity

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Cancer is still one of the leading causes of death worldwide. Many researchers are working to design and develop heterocyclic-based drugs with the potential to treat cancer at various stages. There is always an unmet need to discover new anticancer drugs to treat different types of cancer. Based on literature reports, it was evident that hybrid 1,2,4-triazoles exhibit a wide spectrum of biological potential (particularly potent anticancer activity), as compared to the corresponding monocyclic compounds. In this review, we summarized fused/hybrid 1,2,4-triazole and poly-functionalized 1,2,4-triazoles as anticancer agents. Triazole may be fused with other heterocyclic scaffolds like pyrimidine, pyridine, piperidine, quinoxaline, quinazoline, thiadiazine, indole, phthalazine etc. A clear explanation of the method of synthesis, structure-activity relationship, and in vitro results plus the inhibitory concentration of new molecules are focused on in this review article.

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Section: Discussionmentioning

confidence: 99%

Synthetic and Medicinal Perspective of 1,2,4‐Triazole as Anticancer Agents

Rathod

Kumar

2022

Chemistry & Biodiversity

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“…DMHG is also promising in the creation of bioactive heterocycles (pyrroles, pyrazoles, isoxazoles) that contribute to many drugs [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36] and alkaloids [37][38][39]. The authors of the publication [40] have also developed a strategy for cyclizing UDMH and its glyoxal derivative DMHG into biologically active pyrrole-2-ylpyridines (Figure 3).…”

Section: Dmhg In the Directed Synthesis Of Biologically Active Analog...mentioning

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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“…Formation of precipitate was witnessed that desired pyrrole derivative 12 has been formed. [5] The desired precipitate was filtered, washed and further dried. The scope of reaction was generalized using assorted range of acetophenone having electron withdrawing and releasing group.…”

Section: Synthesis Of Pyrrole Scaffoldmentioning

confidence: 99%

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

Kumar

2020

ChemistrySelect

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p‐tosylmethyl isocyanide (TosMIC) which is also known as van Leusen's reagent hold the three functionalized groups including the isocyanide and sulfonyl group and an alpha carbon which is acidic by nature. Tosyl set of this fortunate reagent acts as a good leaving group and assist the alpha carbon to contribute in a range of cyclization strategies. Exceptionally, TosMIC was also proved as a good sulfonylating and sulfomethylating reagent. TosMIC has proved as a powerful and versatile synthon and betrothed in the synthesis of broad range of heterocycles having pharmacological interest. This review is focused on synthetic utility of TosMIC in diverse range of heterocycles like five membered heterocycles, fused heterocycles, linked or tethered heterocycles, spiro compounds etc. It is also utilized for regio, chemo and stereoselective synthesis and production of sulfones and sulfinates. It serves as an important building block in various synthetic methodologies like multi component reaction, cyclization, domino, cascade and cycloaddition and metal catalysed reactions. Various new catalyst and novel methodologies were explored due to enormous use of this wonderful reagent.

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One-pot synthesis of [4-(tert-butyl)-1H-pyrrol-3-yl](phenyl)methanone from tosylmethyl isocyanide and carbonyl compound

Cited by 14 publications

References 23 publications

Synthetic and Medicinal Perspective of 1,2,4‐Triazole as Anticancer Agents

Synthetic and Medicinal Perspective of 1,2,4‐Triazole as Anticancer 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

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

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