Hypervalent iodine oxidation of phenol derivatives using a catalytic amount of 4-iodophenoxyacetic acid and Oxone® as a co-oxidant

Yakura, Takayuki; Omoto, Masanori; Yamauchi, Yû; Tian, Yuan; Ozono, Ayaka

doi:10.1016/j.tet.2010.04.124

Cited by 65 publications

(48 citation statements)

References 91 publications

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“…Vicinal aliphatic methine protons (δ = 4.83 and 5.26 ppm, 2H, 2d, 3 J HH = 7.2 Hz, MeO 2 C-CH-CH-CO 2 Me) [23][24][25]. In addition, signals due to the two olefinic protons were observed as two singlets (δ = 5.95 and 6.02 ppm, 2 s, 2H, 2CH = CR 3 [26,27]. The 13 C NMR spectrum of 4a showed 28 distinct resonances in agreement with the proposed structure.…”

Section: Resultsmentioning

confidence: 99%

Novel and one‐pot Synthesis of Tetrahydropyrrolo[1,2‐a]‐2‐Methylbenzothiazole‐3‐Spiro‐1^′‐Cyclohexa‐2^′,5^′‐Dien‐4^′‐one‐4,5‐Dicarboxylate Derivatives via a Three Component Reaction

Milani

Nassiri

2016

Journal of Heterocyclic Chem

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The three component condensation reactions involving 2‐methylbenzothiazole or 2,5‐dimethylbenzothiazole, dialkyl acetylenedicarboxylate, and 2,6‐dimethyl phenol or 2,6‐di‐tert‐butylphenol constitute a novel and one‐pot synthesis of tetrahydropyrrolo[1,2‐a]‐2‐methylbenzothiazoles‐3‐spiro‐1′‐cyclohexa‐2′,5′‐dien‐4′‐one‐4,5‐dicarboxylate derivatives in good yields. The reactions proceeded at room temperature without using any catalyst. This method is very useful to functionalize benzothiazole derivatives in a one‐pot operation.

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Section: Resultsmentioning

confidence: 99%

Novel and one‐pot Synthesis of Tetrahydropyrrolo[1,2‐a]‐2‐Methylbenzothiazole‐3‐Spiro‐1^′‐Cyclohexa‐2^′,5^′‐Dien‐4^′‐one‐4,5‐Dicarboxylate Derivatives via a Three Component Reaction

Milani

Nassiri

2016

Journal of Heterocyclic Chem

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“…Oxone has also been used by Yakura et al. for the oxidation of iodine(I) . The experimental procedure used to obtain the reaction products from iodoarenes 1 and arenes 2 is very simple.…”

Section: Methodsmentioning

confidence: 99%

“…[6] Oxone has also been used by Yakura et al for the oxidation of iodine(I). [7] The experimental procedure used to obtain the reactionp roducts from iodoarenes 1 and arenes 2 is very simple. Initially,i odoarene 1 is reactedw ith Oxone in the presence of trifluoroacetic acid to generate [bis(trifluoroacetoxy)iodo]arenes before arene 2 is added to the reaction mixture (method A).…”

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confidence: 99%

Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone

et al. 2016

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“…2,5-Dimethoxyphenylacetic acid was oxidized via a previously reported procedure[40] employing oxone and 4-iodophenoxyacetic acid to the benzoquinone 22 as an orange solid (16.5 mg, 75%) without the need for a purification step.…”

Section: Methodsmentioning

confidence: 99%

Benzoquinones as inhibitors of botulinum neurotoxin serotype A

Bremer

Hixon

Janda

2014

Bioorganic & Medicinal Chemistry

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Although botulinum neurotoxin serotype A (BoNT/A) is known for its use in cosmetics, it causes a potentially fatal illness, botulism, and can be used as a bioterror weapon. Many compounds have been developed that inhibit the BoNTA zinc-metalloprotease light chain (LC), however, none of these inhibitors have advanced to clinical trials. In this study, a fragment-based approach was implemented to develop novel covalent inhibitors of BoNT/A LC. First, electrophilic fragments were screened against BoNT/A LC, and benzoquinone (BQ) derivatives were found to be active. In kinetic studies, BQ compounds acted as irreversible inhibitors that presumably covalently modify cysteine 165 of BoNT/A LC. Although most BQ derivatives were highly reactive toward glutathione in vitro, a few compounds such as natural product naphthazarin displayed low thiol reactivity and good BoNT/A inhibition. In order to increase the potency of the BQ fragment, computational docking studies were employed to elucidate a scaffold that could bind to sites adjacent to Cys165 while positioning a BQ fragment at Cys165 for covalent modification; 2-amino-N-arylacetamides met these criteria and when linked to BQ displayed at least a 20-fold increase in activity to low μM IC50 values. Unlike BQ alone, the linked-BQ compounds demonstrated only weak irreversible inhibition and therefore acted mainly as non-covalent inhibitors. Further kinetic studies revealed a mutual exclusivity of BQ covalent inactivation and competitive inhibitor binding to sites adjacent to Cys165, refuting the viability of the current strategy for developing more potent irreversible BoNT/A inhibitors. The highlights of this study include the discovery of BQ compounds as irreversible BoNT/A inhibitors and the rational design of low μM IC50 competitive inhibitors that depend on the BQ moiety for activity.

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Hypervalent iodine oxidation of phenol derivatives using a catalytic amount of 4-iodophenoxyacetic acid and Oxone® as a co-oxidant

Cited by 65 publications

References 91 publications

Novel and one‐pot Synthesis of Tetrahydropyrrolo[1,2‐a]‐2‐Methylbenzothiazole‐3‐Spiro‐1^′‐Cyclohexa‐2^′,5^′‐Dien‐4^′‐one‐4,5‐Dicarboxylate Derivatives via a Three Component Reaction

Novel and one‐pot Synthesis of Tetrahydropyrrolo[1,2‐a]‐2‐Methylbenzothiazole‐3‐Spiro‐1^′‐Cyclohexa‐2^′,5^′‐Dien‐4^′‐one‐4,5‐Dicarboxylate Derivatives via a Three Component Reaction

Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone

Benzoquinones as inhibitors of botulinum neurotoxin serotype A

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Hypervalent iodine oxidation of phenol derivatives using a catalytic amount of 4-iodophenoxyacetic acid and Oxone® as a co-oxidant

Cited by 65 publications

References 91 publications

Novel and one‐pot Synthesis of Tetrahydropyrrolo[1,2‐a]‐2‐Methylbenzothiazole‐3‐Spiro‐1′‐Cyclohexa‐2′,5′‐Dien‐4′‐one‐4,5‐Dicarboxylate Derivatives via a Three Component Reaction

Novel and one‐pot Synthesis of Tetrahydropyrrolo[1,2‐a]‐2‐Methylbenzothiazole‐3‐Spiro‐1′‐Cyclohexa‐2′,5′‐Dien‐4′‐one‐4,5‐Dicarboxylate Derivatives via a Three Component Reaction

Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone

Benzoquinones as inhibitors of botulinum neurotoxin serotype A

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Novel and one‐pot Synthesis of Tetrahydropyrrolo[1,2‐a]‐2‐Methylbenzothiazole‐3‐Spiro‐1^′‐Cyclohexa‐2^′,5^′‐Dien‐4^′‐one‐4,5‐Dicarboxylate Derivatives via a Three Component Reaction

Novel and one‐pot Synthesis of Tetrahydropyrrolo[1,2‐a]‐2‐Methylbenzothiazole‐3‐Spiro‐1^′‐Cyclohexa‐2^′,5^′‐Dien‐4^′‐one‐4,5‐Dicarboxylate Derivatives via a Three Component Reaction