A synthetic route to 11-(1H-pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline derivatives exploiting a three-component coupling strategy under microwave irradiation

Azizian, Javad; Karimi, Ali Reza; Kazemizadeh, Zahra; Mohammadi, Ali A.; Mohammadizadeh, Mohammad R.

doi:10.1016/j.tetlet.2005.06.099

Cited by 27 publications

(13 citation statements)

References 16 publications

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“…Although the effect of K10 Montmorillonite on the synthesis of quinoxalines under microwave irradiation has been recently reported, 24 acidic alumina shows the highest efficiency for both benzil and acyloin (Table 1, entry 1). In this regard, the acidic alumina was applied for the synthesis of products 1a-h depicted in Table 2.…”

Section: Entry 8)mentioning

confidence: 99%

Benign approaches for the microwave-assisted synthesis of quinoxalines

Mohsenzadeh

Aghapoor

Darabi

2007

J. Braz. Chem. Soc.

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Neste trabalho foram usados dois sistemas simples, rápidos (3 min) e versáteis, de transferência de energia de microondas, na ausência de solventes, para a síntese de quinoxalinas (2,3-difenilquinoxalina e seus derivados, 2,3-difenil-4a,5,6,7,8,8a-hexahidroquinoxalina, 2-fenilquinoxalina, piridina-2,3-diamina e 2,3-dihidro-5,6-difenilpirazina). O primeiro método consiste no uso de suportes minerais na reação de 1,2-dicarbonil (benzil) ou α-hidroxicetona (aciloína) com 1,2-diaminas. Entre os suportes minerais, a eficiência da alumina ácida como catalisador foi claramente comprovada (80-86%). Além disso, apresenta um papel importante na oxidação de aciloína ao correspondente sistema 1,2-dicarbonílico. O segundo método consiste no uso de microondas em mistura dos reagentes 1,2-dicarbonil(benzil) e 1,2-diaminas. O excelente rendimento dos produtos (90-97%) e a simples lavagem com água e filtração na ausência de solventes orgânicos fazem desse sistema uma ótima alternativa para a prevenção de poluição, em um processo ambientalmente benigno. Embora os dois métodos tenham sido planejados para evitar passos adicionais de purificação, o último é um processo mais limpo com tratamento reacional mais simples.Two benign, simple, rapid (3 min), solvent-free and versatile microwave energy transfer systems for the synthesis of quinoxalines, i.e. 2,3-diphenylquinoxaline and its derivatives, 2,3-diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline, and 2-phenylquinoxaline and also pyridine-2,3-diamine and 2,3-dihydro-5,6-diphenylpyrazine have been used. The first approach consists on the use of mineral supports on the reaction of 1,2-dicarbonyl (benzil) or α-hydroxyketone (acyloin) with 1,2-diamines. Among mineral supports, the efficiency of acidic alumina as catalyst was clearly proved (80-86%). Moreover, it has an oxidative role in the tandem oxidation of acyloin to the corresponding 1,2-dicarbonyl. The second approach is the use of polar paste system on the reaction of 1,2-dicarbonyl (benzil) with 1,2-diamines. The excellent products yield (90-97%) and simple washing with water and filtration in the absence of organic solvent makes it an impressive alternative green platform. Although both methods implemented in this study have been designed to circumvent additional purification steps, the latter is cleaner with an easier work-up.

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Section: Entry 8)mentioning

confidence: 99%

Benign approaches for the microwave-assisted synthesis of quinoxalines

Mohsenzadeh

Aghapoor

Darabi

2007

J. Braz. Chem. Soc.

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“…In continuation of our previous work on the synthesis of heterocyclic compounds and MCRs [19][20][21][22][23][24][25][26][27], we wish to report a novel, efficient, one-pot, three-component method for the preparation of 1-aryl-N,N-dimethyl-1H-naphtho[1,2-e] [1,3]oxazine-3-amine derivatives under MWassisted conditions.…”

Section: Introductionmentioning

confidence: 99%

An efficient Biginelli one-pot synthesis of new naphthalene-condensed oxazine derivatives under microwave-assisted conditions

et al. 2012

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“…[16][17][18] Several methods have been reported for the synthesis of quinoxaline derivatives using solid supports and microwave-assisted reactions. [19][20][21][22][23][24] The aim of this study was the synthesis of new ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives on solid supports such as silica gel, florisil, alumina, 4Å molecular sieves, montmorillonite KSF, and montmorillonite K10, by room temperature and microwave-assisted solvent-free procedures (Figure 3), as a strategy to enhance yield and reduce the reaction time as a part of our ongoing research in the design and synthesis of new compounds with potential pharmacological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of quinoxaline 1,4-di-N-oxide derivatives on solid support using room temperature and microwave-assisted solvent-free procedures

Gómez-Caro¹,

Sánchez-Sánchez²,

Bocanegra-García³

et al. 2011

Quím. Nova

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Recebido em 19/8/10; aceito em 16/2/11; publicado na web em 15/4/11We describe the synthesis of 12 new ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives on solid supports with room temperature and microwave-assisted solvent-free procedures. Results show that solid supports have good catalytic activity in the formation of quinoxaline 1,4-di-N-oxide derivatives. We found that florisil and montmorillonite KSF and K10 could be used as new, easily available, inexpensive alternatives of catalysts. Additionally, room temperature and microwave-irradiation solvent-free synthesis was more efficient than a conventional procedure (Beirut reaction), reducing reaction time and increasing yield.

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A synthetic route to 11-(1H-pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline derivatives exploiting a three-component coupling strategy under microwave irradiation

Cited by 27 publications

References 16 publications

Benign approaches for the microwave-assisted synthesis of quinoxalines

Benign approaches for the microwave-assisted synthesis of quinoxalines

An efficient Biginelli one-pot synthesis of new naphthalene-condensed oxazine derivatives under microwave-assisted conditions

Synthesis of quinoxaline 1,4-di-N-oxide derivatives on solid support using room temperature and microwave-assisted solvent-free procedures

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