An efficient synthesis of bis(indolyl) methanes and N,N′-alkylidene bisamides by Silzic under solvent free conditions

Soliman, Hanan A.; Mubarak, Ahmed Y.; Elmorsy, Saad S.

doi:10.1016/j.cclet.2015.11.013

Cited by 31 publications

(2 citation statements)

References 36 publications

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“…Silica gel is an intriguing solid support, since it is a low cost, commercially available and non-hazardous support, that can be employed in tandem with various traditional catalysts [70]. Some examples in literature are ZrOCl 2 •8H 2 O/SiO 2 [71], P 2 O 5 /SiO 2 [72], LiHSO 4 /SiO 2 [73], (PhCH 2 PPh 3 ) + Br − /SiO 2 [74], H 2 SO 4 /SiO 2 [75], ZnCl 2 /SiO 2 [76], heteropoly-11-tungsto-1-vanadophosphoric acid, H4[PVV W11O40] (HPV) (20%) supported on natural clay (HPVAC-20) [77], V 2 O 5 /SiO 2 [78], strongly acidic cation exchange resin (Seralite SRC-120) [79] or HCl/SiO 2 [80]. Among all the protocols mentioned above, it is worth mentioning that Hojati et al, in 2013, developed a simple, novel and efficient procedure for the synthesis of BIMs, utilizing 1,3dibromo-5,5-dimethylhydantoin (DBDMH) as the catalyst (Scheme 3).…”

Section: Green and Sustainable Approachesmentioning

confidence: 99%

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Kolagkis,

Galathri,

Kokotos

2024

Beilstein J. Org. Chem.

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The synthesis of indoles and their derivatives, more specifically bis(indolyl)methanes (BIMs), has been an area of great interest in organic chemistry, since these compounds exhibit a range of interesting biological and pharmacological properties. BIMs are naturally found in cruciferous vegetables and have been shown to be effective antifungal, antibacterial, anti-inflammatory, and even anticancer agents. Traditionally, the synthesis of BIMs has been achieved upon the acidic condensation of an aldehyde with indole, utilizing a variety of protic or Lewis acids. However, due to the increased environmental awareness of our society, the focus has shifted towards the development of greener synthetic technologies, like photocatalysis, organocatalysis, the use of nanocatalysts, microwave irradiation, ball milling, continuous flow, and many more. Thus, in this review, we summarize the medicinal properties of BIMs and the developed BIM synthetic protocols, utilizing the reaction between aldehydes with indoles, while focusing on the more environmentally friendly methods developed over the years.

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Section: Green and Sustainable Approachesmentioning

confidence: 99%

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Kolagkis,

Galathri,

Kokotos

2024

Beilstein J. Org. Chem.

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“…with aldehydes (1 eq.). Various catalysts have been reported for this synthesis, such as hydroxyapatite [28], phosphotungstic acid [29] [32], NiFe 2 O 4 @SiO 2 -PPA [33], CH 3 COCl [34], HPVAC-20 (heteropoly-11-tungsto-1vanadophosphoric acid supported on activated natural clay) [35], ZnCl 2 /SiO 2 [36] and sulfonated carbon/nanotitania composite (C/TiO 2 -SO 3 H) [37]. Nevertheless, many of the reported methods have restrictions such as, for example, long reaction times, moderate yields, harsh reaction conditions and the utilization of volatile and harmful organic solvents.…”

Section: Introductionmentioning

confidence: 99%

N,N,N′,N′-Tetramethylethylene-diaminium-N,N′-disulfonic acid trifluoroacetate and pyridinium-N-sulfonic acid hydrogen sulfate as highly effective dual-functional catalysts for the preparation of N,N′-alkylidene bisamides

Kordrostami

Zare

Karami

2019

Zeitschrift Für Naturforschung B

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In this research, Brønsted-acidic ionic liquids N,N,N′,N′-tetramethylethylene-diaminium-N,N′-disulfonic acid trifluoroacetate ([TMEDSA][TFA]2) and pyridinium-N-sulfonic acid hydrogen sulfate ([Py-SO3H][HSO4]) have been introduced as dual-functional catalysts for the green, simple and effective preparation of N,N′-alkylidene bisamides by the reaction of primary amides (2 eq.) with arylaldehydes (1 eq.) under solvent-free conditions. The reaction results and conditions of the catalysts have been compared with the previously reported ones. [TMEDSA][TFA]2 and [Py-SO3H][HSO4] were superior to the previously reported catalysts in terms of two or more of these factors: reaction times (10–45 min), yields (86–98%), temperature and the reaction conditions. Additionally, a plausible and attractive mechanism based on dual functionality of the catalysts has been proposed.

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ZnCl₂ supported on Fe₃O₄@SiO₂ core–shell nanocatalyst for the synthesis of quinolines via Friedländer synthesis under solvent‐free condition

Soleimani

Namivandi

Sepahvand

2016

Applied Organom Chemis

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A magnetic nanocatalyst of Fe3O4@SiO2/ZnCl2 was prepared by supporting ZnCl2 on silica‐coated magnetic nanoparticles of Fe3O4. This recoverable catalyst was used for the synthesis of quinolines via Friedländer synthesis from 2‐aminoaryl ketones and α‐methylene ketones under solvent‐free condition. The prepared catalyst was characterized by FT‐IR, TEM, SEM, XRD, EDX, ICP‐OES, VSM and BET. It was found that Fe3O4@SiO2/ZnCl2 showed higher catalytic activity than homogenous ZnCl2, and could be reused several times without significant loss of activity.

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An efficient synthesis of bis(indolyl) methanes and N,N′-alkylidene bisamides by Silzic under solvent free conditions

Cited by 31 publications

References 36 publications

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

N,N,N′,N′-Tetramethylethylene-diaminium-N,N′-disulfonic acid trifluoroacetate and pyridinium-N-sulfonic acid hydrogen sulfate as highly effective dual-functional catalysts for the preparation of N,N′-alkylidene bisamides

ZnCl₂ supported on Fe₃O₄@SiO₂ core–shell nanocatalyst for the synthesis of quinolines via Friedländer synthesis under solvent‐free condition

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An efficient synthesis of bis(indolyl) methanes and N,N′-alkylidene bisamides by Silzic under solvent free conditions

Cited by 31 publications

References 36 publications

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

N,N,N′,N′-Tetramethylethylene-diaminium-N,N′-disulfonic acid trifluoroacetate and pyridinium-N-sulfonic acid hydrogen sulfate as highly effective dual-functional catalysts for the preparation of N,N′-alkylidene bisamides

ZnCl2 supported on Fe3O4@SiO2 core–shell nanocatalyst for the synthesis of quinolines via Friedländer synthesis under solvent‐free condition

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ZnCl₂ supported on Fe₃O₄@SiO₂ core–shell nanocatalyst for the synthesis of quinolines via Friedländer synthesis under solvent‐free condition