Metal-free synthetic approaches to 1,5-disubstituted 1,2,3-triazoles

Malkova, K. V.; Bubyrev, Andrey; Saeed, Aamer; Dar’in, Dmitry; Krasavin, Mikhail

doi:10.1016/j.tetlet.2022.154228

Cited by 6 publications

(2 citation statements)

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“…Further development led to the use of activated dipolarophiles such as enamines, enolates, or alkenes to accelerate the 1,3-dipolar cycloaddition with alkyl or aryl azides, as well as to synthesize a diazo imine intermediate using the Regitz diazo-transfer reagent for Dimorth cyclization. Nonetheless, the restriction of the activating groups (carbonyl or aryl moieties are required at the 4- or 5-position) limits the aforementioned protocols for generating 1,4,5-TTs (Scheme b,c). − , Furthermore, a lack of regioselectivity is observed with asymmetrical ketones (Scheme d)…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism

Chi,

Yang,

Hung

et al. 2024

J. Org. Chem.

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A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4-and 1,5disubstituted and 1,4,5-trisubstituted triazoles can be regio-and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4phosphonate byproducts, which is aligned with crystallographic and experimental evidence.

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Section: Introductionmentioning

confidence: 99%

“…Nonetheless, the restriction of the activating groups (carbonyl or aryl moieties are required at the 4- or 5-position) limits the aforementioned protocols for generating 1,4,5-TTs ( Scheme 1 b,c). 5a − 5d , 8 Furthermore, a lack of regioselectivity is observed with asymmetrical ketones ( Scheme 1 d). 5f…”

Section: Introductionmentioning

confidence: 99%