Dimroth-type N/S-interchange of <i>N</i>-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-<i>d</i>]thiazolones

Vinogradova, Ekaterina E.; Газиева, Галина А.; Izmest’ev, Alexei N.; Карноухова, Валентина А.; Кравченко, Ангелина Н.

doi:10.1039/d1ra05568b

Cited by 6 publications

(1 citation statement)

References 32 publications

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“…Michael adducts [12,13], S-alkyl [14,15], S-alkenyl [16], S-alkynyl [17][18][19] derivatives can act as such S-substituted substrates. Fused thiazoles have also been prepared by acid-catalyzed Dimrothtype rearrangement of N-aminothioglycolurils [20].…”

Section: Introductionmentioning

confidence: 99%

One‐pot regioselective synthesis of new imidazo[4,5‐e]thiazolo[3,2‐b][1,2,4]triazines by reaction of imidazotriazines with propargyl bromide

Vinogradova

Кравченко

Газиева

2023

Journal of Heterocyclic Chem

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A regioselective one‐pot method for the synthesis of imidazo[4,5‐e]thiazolo[3,2‐b][1,2,4]triazine derivatives has been developed by the reaction of imidazotriazinethiones with propargyl bromides upon treatment with potassium carbonate in methanol. The synthesis was accomplished by converting the imidazotriazinethiones into S‐propargyl derivatives followed by subsequent 5‐exo‐dig cyclization. The mechanism of the cyclization was studied using deuterium labels.

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Section: Introductionmentioning

confidence: 99%

One‐pot regioselective synthesis of new imidazo[4,5‐e]thiazolo[3,2‐b][1,2,4]triazines by reaction of imidazotriazines with propargyl bromide

Vinogradova

Кравченко

Газиева

2023

Journal of Heterocyclic Chem

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Triple‐Purpose Thiocyanate‐Containing Protic Ionic Liquids: Chemodivergent Transformations of Dihydroimidazolones into Imidazo[4,5‐d]Oxazolethiones and Imidazo[4,5‐d]Thiazolones

Ratmanova,

Ermolaev,

Baranov

et al. 2024

Asian J Org Chem

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Triple‐purpose protic ionic liquids were employed as a solvent, a Brønsted acid catalyst, and a source of the nucleophile (thiocyanate‐ion) for the chemodivergent transformation of dihydroimidazolones into 2‐thioxohexahydro‐5H‐imidazo[4,5‐d]oxazol‐5‐ones and tetrahydro‐2H‐imidazo[4,5‐d]thiazole‐2,5(3H)‐diones. An important feature of this process is the switching of its chemoselectivity by simple variation of the reaction temperature, other conditions being the same; this allowed both types of products to be obtained selectively. Straightforward aqueous work‐up of reaction mixture provided crystalline bicyclic products in pure form in an environmentally friendly manner.

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Construction of New Heterocyclic System, Imidazo[4,5‐d]thiazolo[4,3‐b]oxazole, via Cascade Reaction of Thioglycolurils with α‐Bromoketones

Vinogradova,

Karnoukhova,

Kravchenko

et al. 2024

Asian J Org Chem

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A method for the synthesis of new heterocyclic system representatives, i.e. imidazo[4,5‐d]thiazolo[4,3‐b]oxazole derivatives, by the reaction of thioglycolurils with α‐bromoketones has been developed. The reaction includes a cascade one‐pot S‐alkylation/nucleophilic addition/ring‐opening/ring‐closing process. This protocol is compatible with a broad scope of α‐bromoketones, diastereoselectively affording diverse products with 3aS*,4aR*,8aR*‐imidazo[4,5‐d]thiazolo[4,3‐b]oxazole core in 40–76% yields.

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Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones

Abstract: An original method for the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolone derivatives has been developed based on an acid-induced Dimroth-type N/S-interchange of N-aminothioglycolurils formed in situ into 2-hydrazonoimidazo[4,5-d]thiazolones.

Cited by 6 publications

References 32 publications

One‐pot regioselective synthesis of new imidazo[4,5‐e]thiazolo[3,2‐b][1,2,4]triazines by reaction of imidazotriazines with propargyl bromide

One‐pot regioselective synthesis of new imidazo[4,5‐e]thiazolo[3,2‐b][1,2,4]triazines by reaction of imidazotriazines with propargyl bromide

Triple‐Purpose Thiocyanate‐Containing Protic Ionic Liquids: Chemodivergent Transformations of Dihydroimidazolones into Imidazo[4,5‐d]Oxazolethiones and Imidazo[4,5‐d]Thiazolones

Construction of New Heterocyclic System, Imidazo[4,5‐d]thiazolo[4,3‐b]oxazole, via Cascade Reaction of Thioglycolurils with α‐Bromoketones

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