A rapid and efficient microwave-assisted synthesis of hydantoins and thiohydantoins

Muccioli, Giulio G.; Poupaert, Jacques H.; Wouters, Johan; Norberg, Bernadette; Poppitz, Wolfgang; Scriba, Gerhard K. E.; Lambert, Didier M.

doi:10.1016/s0040-4020(03)00033-4

Cited by 97 publications

(55 citation statements)

References 22 publications

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“…the Biltz synthesis to obtain phenytoin. 17,23 Biltz reported that the reaction of N-methylurea with benzil resulted in formation of 5,5-diphenylhydantoin.…”

Section: Resultsmentioning

confidence: 99%

The use of benzil to obtain functionalized N-heterocycles

Braibante¹,

Braibante²,

Uliana³

et al. 2008

J. Braz. Chem. Soc.

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Neste trabalho foi estudada a reatividade da benzila, empregando-se C,N-e N,N-nucleófilos tais como 2-butenoatos de etila 3-amino substituidos 4a-c, (S,Z)-3-(1-etóxi-3-hidróxi-1-oxo-2-propanilamina)-2-butenoato de etila 6, semicarbazida 8 e tiossemicarbazida 10, para avaliar os centros eletrofílicos na formação de compostos heterocíclicos polifuncionalizados, obtendo-se pirrolinonas 5a-c, pirrol 7, triazinona 9 e triazintiona 11. A dibenzoila 3 empregada foi obtida pela oxidação da benzoina na ausência de solvente em um estudo comparativo entre diferentes protocolos de oxidação, utilizando suportes sólidos associados ou não a energia de microondas com bons rendimentos sem empregar reagentes agressivos.In this work, the reactivity of benzil was studied, employing C,N-and N,N-nucleophiles, such as ethyl(3-amino substituted) 2-butenoates 4a-c , (S,Z)-ethyl 3-(1-ethoxy-3-hydroxy-1-oxopropan-2-ylamino)but-2-enoate 6, semicarbazide 8 or thiosemicarbazide 10, to evaluate their electrophilic centers as building blocks for the synthesis of the polyfunctionalized heterocyclic compounds, resulting in pyrrolinone 5a-c, pyrrole 7, triazinone 9 and triazinethione 11. The employed benzil 3 was obtained by the oxidation of the benzoin under solvent free conditions in a comparative study between different protocols of oxidation, using the methodology under mild reaction conditions and supported reagent associated to the microwave irradiation, with good results and without aggressive reagents.

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“…the Biltz synthesis to obtain phenytoin. 17,23 Biltz reported that the reaction of N-methylurea with benzil resulted in formation of 5,5-diphenylhydantoin.…”

Section: Resultsmentioning

confidence: 99%

The use of benzil to obtain functionalized N-heterocycles

Braibante¹,

Braibante²,

Uliana³

et al. 2008

J. Braz. Chem. Soc.

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“…Besides conventional multi-OALibJ | DOI:10.4236/oalib. 1100705 2 October 2014 | Volume 1 | e705 step methods, one-pot, solid-phase and microwave-assisted approaches have been published [7]- [11]. As a part of our current studies on the development of new routes in heterocyclic synthesis [12]- [14], we now report here a novel and efficient method for the solid-phase synthesis of imidazolidine-2-thiones 3, hydantoins and thiohydantoin 4.…”

Section: Introductionmentioning

confidence: 94%

One-Pot Synthesis of Imidazolidine-2-Thiones, Hydantoins and Thiohydantoins under Solvent-Free and Grinding Conditions

Ghanbari¹,

Safari²,

Roohi³

2014

OALib

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A convenient, environmentally friendly and mild green synthesis of imidazolidine-2-thiones, hydantoin and thiohydantoin derivatives was developed by the one-pot reaction of benzils, urea or thiourea derivatives, and strong base at with grinding. The key advantages are the short reaction times, excellent yields, simple workup, and easy purification in the solvent-free condition. The present method aimed to overcome the limitations and drawbacks of the reported methods such as hard work-up, low yield, hazardous solvent and long reaction time.

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“…9 Mais recentemente, Muccioli e colaboradores 10 reportaram uma adaptação da síntese de Biltz com o uso de micro-ondas, permitindo a formação tanto de hidantoínas quanto de tio-hidantoínas de maneira mais rápida e limpa, características estas comuns de reações por micro-ondas. Neste estudo, o uso de diferentes solventes foi primeiramente testado, de maneira que os sistemas DMSO e dioxano/H 2 O (2:5 v:v) promoveram um maior rendimento e seletividade para a reação.…”

Section: Introductionunclassified