Metal-Free Three-Component Domino Approach to Phosphonylated Triazolines and Triazoles

Ahamad, Shakir; Kant, Ravi; Mohanan, Kishor

doi:10.1021/acs.orglett.5b03437

Cited by 57 publications

(27 citation statements)

References 71 publications

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“…In this context, our group took a step forward, where in 2016, we disclosed the first application of BOR in the preparation of phosphonylated triazolines and triazoles via a multicomponent domino strategy. [31] The reaction between aldehyde 17, primary amine 29, and BOR 2 in methanol afforded the trans-1,4,5-trisubstituted 1,2,3-triazolines 30 with exclusive diastereoselectivity. The reaction's outcome revealed that the Schiff base formation and the following 1,3 dipolar cycloaddition were faster than the undesired aldehyde homologation.…”

Section: Synthesis Of Triazolines and Triazolesmentioning

confidence: 99%

The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

Jamali

Vaishanv

Mohanan

2020

The Chemical Record

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Azaheterocycles are one of the most prevalent classes of compounds present in numerous bioactive compounds, natural products, and agrochemicals, and undoubtedly, new methods to access them are always in high demand. Among the methods available, the 1,3dipolar cycloaddition reactions involving diazo compounds are particularly attractive because of their ability to rapidly construct densely functionalized azaheterocycles in a regioselective manner. In this context, the Bestmann-Ohira reagent has become a well-known reagent for the 1,3dipolar cycloaddition reactions to produce phosphonylated heterocycles, besides its widespread use as a homologating agent for the conversion of aldehydes to alkynes. This account details our efforts toward broadening the synthetic utility of the Bestmann-Ohira reagent and related compounds for the preparation of azaheterocycles such as pyrazoles, spirooxindoles, triazoles, triazolines, and spiropyrazolines, emphasizing on domino multicomponent reactions employing readily available feedstock reagents.

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Section: Synthesis Of Triazolines and Triazolesmentioning

confidence: 99%

The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

Jamali

Vaishanv

Mohanan

2020

The Chemical Record

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“…Proposed mechanism for the Ag-catalyzed cycloaddition reactions More recently, a general and straightforward approach for the facile synthesis of phosphonylated triazoles was achieved by Mohanan and co-workers (Scheme 27). [86] The three-component domino reaction employed readily available aldehydes, amines, and the Bestmann-Ohira reagent (dimethyl α-diazo-β-oxopropylphosphonate) as starting materials and a wide range of 1,4,5-trisubstituted 1,2,3-triazolines and triazoles were assembled under mild conditions. The reaction presumably proceeded through a domino-condensation/1,3-dipolar cycloaddition sequence, in which dimethyl (diazomethyl)phosphonate anion could be in-situ formed from Bestmann-Ohira reagent to react with the Schiff base from the condensation of aldehyde and amine.…”

Section: Scheme 26mentioning

confidence: 99%

Recent Developments in Azide‐Free Synthesis of 1,2,3‐Triazoles

et al. 2017

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1,2,3‐Triazoles, as one of the most significant nitrogen‐containing heterocycles due to their extensive use in biology, material science and organic synthesis, have aroused great interest. 1,2,3‐Triazoles are commonly synthesized by metal‐catalyzed azide–alkyne cycloaddition and organocatalytic azide–carbonyl cycloaddition, which indispensably employ the toxic and potentially explosive azides. The azide‐free synthetic approaches provide a powerful and straightforward alternative to the assembly of diverse 1,2,3‐triazoles without the use of azides. In this review, we summarize the recent development of the construction of 1,2,3‐triazoles under azide‐free conditions.

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“…Several examples were reported on the preparation of 1,2,3-triazol-4-yl-phosphonates by domino or three-component reactions [33,34], however, to the best of our knowledge, only one example mentions the multicomponent synthesis of 1,2,3-triazol-5-yl-phosphonates [20]. Li and co-workers carried out the domino reaction of terminal alkynes, azides, and diethyl-, diisopropyl-or dibenzyl phosphite in the presence of copper(I) chloride as the catalyst (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In Vitro Cytotoxicity and Antibacterial Activity of Novel 1,2,3-Triazol-5-yl-Phosphonates

et al. 2020

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Novel 1,2,3-triazol-5-yl-phosphonates were prepared by the copper(I)-catalyzed domino reaction of phenylacetylene, organic azides and dialkyl phosphites. The process was optimized on the synthesis of the dibutyl (1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)phosphonate in respect of the catalyst, the base and the solvent, as well as of the reaction parameters (molar ratio of the starting materials, atmosphere, temperature and reaction time). The method elaborated could be applied to a range of organic azides and dialkyl phosphites, which confirmed the large scope and the functional group tolerance. The in vitro cytotoxicity on different cell lines and the antibacterial activity of the synthesized 1,2,3-triazol-5-yl-phosphonates was explored. According to the IC50 values determined, only modest antibacterial effect was detected, while some derivatives showed moderate activity against human promyelocytic leukemia HL-60 cells.

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Metal-Free Three-Component Domino Approach to Phosphonylated Triazolines and Triazoles

Cited by 57 publications

References 71 publications

The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

Recent Developments in Azide‐Free Synthesis of 1,2,3‐Triazoles

Synthesis and In Vitro Cytotoxicity and Antibacterial Activity of Novel 1,2,3-Triazol-5-yl-Phosphonates

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