Catalyst-free synthesis of octahydroacridines using glycerol as recyclable solvent

Nascimento, José Edmilson R.; Barcellos, Angelita M.; Sachini, Maraísa; Perin, Gelson; Lenardão, Eder J.; Alves, Diego; Jacob, Raquel G.; Missau, Fabiana

doi:10.1016/j.tetlet.2011.03.045

Cited by 29 publications

(14 citation statements)

References 32 publications

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“…57 Nosso grupo de pesquisa desenvolveu várias metodologias eficientes e sustentáveis para a síntese destes compostos, partindo do (R)-citronelal 1 presente no OE de citronela. [57][58][59] Uma delas consiste em reagir o (R)-citronelal 1 com anilinas 9a-f, na presença de SiO 2 /ZnCl 2 (10 %), na ausência de solvente e utilizando irradiação de micro-ondas (280 W) como fonte de energia (Esquema 6). 57 O produto obtido é constituído de uma mistura de cisoctaidroacridina 8a-f e de seus isômeros trans 8'a-f. A estereosseletividade da reação é dependente da natureza dos substituintes presentes no anel aromático das anilinas.…”

Section: Citronelalunclassified

“…59 Neste protocolo, a mistura de (R)-citronelal 1 e da anilina 9 desejada em glicerol foi aquecida na temperatura de 90 ºC, por períodos que variaram de 7 h a 21 h, dependendo da anilina utilizada (Esquema 8). 59 Os respectivos produtos foram obtidos com rendimentos que variaram de 75 a 98 % e em alguns casos com maior seletividade para os isômeros trans 8'.…”

Section: Esquemaunclassified

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Essential Oils as a Sustainable Raw Material for the Preparation of Products with Higher Value-Added

Jacob

2017

Rev. Virtual Quim.

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Abstract:The use of renewable feedstocks, which may substitute those derived from petroleum, is currently a great challenge in the chemical and pharmaceutical industries. However, plant essential oils (EOs) that have been studied for their biological activities, such as antioxidant, antimicrobial, antifungal and antinociceptive are generally regarded as safe additives maintaining the microbiological stability of foods. EOs are a mixture of natural volatile compounds, that are predominantly formed during the secondary metabolism in plants and commonly concentrated in the leaves, bark or fruits of aromatic plants. They are complex mixtures composed mainly of terpenes (hydrocarbons or oxygenated compounds) and phenylpropanoids, which can be used as a source of raw materials for fine chemicals industry. In recent years, researchers and industries have been focusing on the major compounds of EOs in order to use them as solvents or as bio-based building blocks adding value to this material derived from biomass.Keywords: Essential oil; bio-based compounds; biomass. ResumoO uso de matérias-primas renováveis, que podem substituir os derivados de petróleo, é atualmente um grande desafio para as indústrias químicas e farmacêuticas. No entanto, os óleos essenciais (OEs) de plantas que têm sido estudados pelas suas atividades biológicas, tais como antioxidante, antimicrobiana, antifúngica e antinociceptiva, são geralmente considerados como aditivos seguros para a manutenção da estabilidade microbiológica de alimentos. Os OEs são uma mistura de compostos voláteis naturais, que são formados durante o metabolismo secundário das plantas e geralmente concentrados nas folhas, casca ou frutos de plantas aromáticas. Eles são misturas complexas compostas principalmente de terpenos (hidrocarbonetos ou compostos oxigenados) e fenilpropanoides, que podem ser utilizados como uma fonte de matéria-prima para a indústria de química fina. Nos últimos anos, pesquisadores e indústrias estão focados nos componentes majoritários dos OEs, a fim de usá-los como solventes ou como blocos de construção de base biológica agregando valor a este material derivado de biomassa.

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Section: Citronelalunclassified

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Essential Oils as a Sustainable Raw Material for the Preparation of Products with Higher Value-Added

Jacob

2017

Rev. Virtual Quim.

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“…In addition to this it does not distort the environmental processes. Not a long time ago, it was found that glycerol has been used for Heck and Suzuki coupling [26][27][28], Michael addition [29], Fridel-Crafts type addition, epoxide ring opening [30], synthesis of xanthenes [31] and very recently for the production of benzodiazepines and octahydroacridines [32,33]. Understanding the magnanimity of both 1,4-DHP's and glycerol, a new clean and green protocol has been discussed.…”

Section: Introductionmentioning

confidence: 99%

One-pot, multicomponent synthesis of symmetrical Hantzsch 1,4-dihydropyridine derivatives using glycerol as clean and green solvent

Sohal

Goyal

Sharma³

et al. 2014

Eur. J. Chem.

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“…Further with the present emphasis and increasing demand of biodiesel, which is responsible for the excess production of glycerol as by-product, triggered the discovery of processes that use glycerol for the synthesis of value added chemicals, as reaction medium and for other applications [13][14][15][16][17][18][19]. Recently glycerol has been used for Heck and Suzuki coupling [20][21][22], Michael addition [23], Fridel-Crafts type addition, epoxide ring opening [24], synthesis of xanthenes [25] and very recently for the production of benzodiazepines and octahydroacridines [26,27].…”

Section: Introductionmentioning

confidence: 99%

Glycerol mediated, one pot, multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles

Sohal¹,

Goyal²,

Sharma³

et al. 2013

Eur. J. Chem.

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Catalyst-free synthesis of octahydroacridines using glycerol as recyclable solvent

Cited by 29 publications

References 32 publications

Essential Oils as a Sustainable Raw Material for the Preparation of Products with Higher Value-Added

Essential Oils as a Sustainable Raw Material for the Preparation of Products with Higher Value-Added

One-pot, multicomponent synthesis of symmetrical Hantzsch 1,4-dihydropyridine derivatives using glycerol as clean and green solvent

Glycerol mediated, one pot, multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles

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