The use of aqueous potassium dichloroiodate for the synthesis of ureas

Viana, Gil Mendes; Aguiar, Lúcia Cruz de Sequeira; Ferrao, Jonas de Araujo; Simas, Alessandro B. C.; Vasconcelos, Marcela Guariento

doi:10.1016/j.tetlet.2012.12.045

Cited by 21 publications

(11 citation statements)

References 23 publications

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“…Continuing our interest in the chemistry of trihaloisocyanuric acids 19 and the preparation of new urea derivatives, 10,11,20 we decided to investigate the iodination reaction of substituted N-phenylureas using iodine/TCCA.…”

Section: Figure 1 Trihaloisocyanuric Acids (Txca)mentioning

confidence: 99%

“…When the product did not precipitate, the aqueous mixture was extracted with EtOAc (3 × 10 mL), dried (anhyd Na 2 SO 4 ), and filtered, and the solvent evaporated under reduced pressure to give the desired product. 10 Pale rose powder; yield: 57 mg (87%); mp 200 °C (dec.); R f = 0.06 (EtOAc/hexane, 1:1). IR (KBr): 3427, 3306, 3216, 1654, 1611, 1588, 1578, 1545, 1482, 1355 10 White powder; yield: 73 mg (92%); mp 187-188 °C; R f = 0.51 (EtOAc/ hexane, 1:1).…”

Section: Substituted N-(4-iodophenyl)ureas 2a-m; General Proceduresmentioning

confidence: 99%

“…9c,d They are also useful synthetic intermediates in metal-catalyzed (Suzuki, Heck, Sonogashira, and related) C-C and C-N cross-coupling reactions that aim to prepare more complex molecules bearing a urea moiety. 10,11 Recently, we reported a green SuzukiMiyaura cross-coupling reaction of N-(4-iodophenyl)ureas using palladium nanoparticles stabilized by cyclodextrins to produce a series of new biphenylureas 11 with potential use in medicinal chemistry. 12 To the best of our knowledge, there is not a protocol for the direct iodination of N-phenylureas described in the literature.…”

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confidence: 99%

“…9a,b,14 Interested in the synthesis of symmetrical and unsymmetrical ureas, our group reported an easy and efficient method for the preparation of substituted ureas by oxidation of thioureas with aqueous KICl 2 (~2 M, pH 3). 10 Moreover, by simply changing the reaction conditions to reflux, N-arylthioureas undergo sequential oxidation and aryl group iodination. 10 This protocol is effective to obtain N-(4-iodophenyl)urea N′,ureas could not be obtained as mostly hydrolyzed products were observed (4-iodoaniline).…”

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confidence: 99%

“…10 Moreover, by simply changing the reaction conditions to reflux, N-arylthioureas undergo sequential oxidation and aryl group iodination. 10 This protocol is effective to obtain N-(4-iodophenyl)urea N′,ureas could not be obtained as mostly hydrolyzed products were observed (4-iodoaniline). Therefore, the search for a new methodology employing mild and neutral conditions to circumvent this inconvenience is of great interest.…”

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confidence: 99%

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Highly Regioselective Iodination of N-Phenylureas with Iodine/Trichloroisocyanuric Acid

et al. 2016

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Section: Figure 1 Trihaloisocyanuric Acids (Txca)mentioning

confidence: 99%

Section: Substituted N-(4-iodophenyl)ureas 2a-m; General Proceduresmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Highly Regioselective Iodination of N-Phenylureas with Iodine/Trichloroisocyanuric Acid

et al. 2016

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Highly Efficient Curtius Rearrangement Approach for the Synthesis of Unsymmetrical Sulfonimidoyl Ureas

et al. 2017

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Ah ighly efficient synthesis of unsymmetrical sulfoximineu reas is developed. Ther eactionu nites simple NH-sulfoximines and acyl azides by af ormal Curtius rearrangementa st he key step. This reaction could be easily scaled up to gram scale and omits the generation of hazardous byproducts, thusa llowing ap ractical and environmentally benignp ath for the synthesis of medicinally important sulfonimidoyl unsymmetrical ureas.

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Selectivity Studies Towards the Synthesis of Novel Biaryl Ureas by (Hetero)Nanocatalysis: Size Control and Support Effects

et al. 2015

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A series of novel biaryl ureas containing different structural patterns have been prepared in good yields in the presence of palladium nanoparticles (PdNPs) with narrow particle size distribution. In particular, α, β‐, and γ‐hydroxypropylated cyclodextrins were used as reductants/stabilizers under different Pd‐to‐cyclodextrin ratios to tune the particle size and exploit the surface/cavity effects in the Suzuki–Miyaura reaction. Catalyst recovery in this process was pursued as well. Owing to its excellent performance, ceria was explored as a support for these PdNPs. The heterogeneous catalyst was characterized and investigated in the reaction of N‐(4‐iodo‐aryl),N′‐alkyl urea and phenylboronic acid. Our preliminary results revealed a high activity of the catalyst at 0.5 mol % Pd0 during three consecutive cycles. It is suggested that the specific interface between Pd0 and the high‐surface‐area ceria has a role in the catalytic performance.

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The use of aqueous potassium dichloroiodate for the synthesis of ureas

Cited by 21 publications

References 23 publications

Highly Regioselective Iodination of N-Phenylureas with Iodine/Trichloroisocyanuric Acid

Highly Regioselective Iodination of N-Phenylureas with Iodine/Trichloroisocyanuric Acid

Highly Efficient Curtius Rearrangement Approach for the Synthesis of Unsymmetrical Sulfonimidoyl Ureas

Selectivity Studies Towards the Synthesis of Novel Biaryl Ureas by (Hetero)Nanocatalysis: Size Control and Support Effects

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