A green protocol for the synthesis of bis(indolyl)methanes catalyzed by succinic acid under microwave irradiation

Nasreen, Aayesha; Varala, Ravi; Rao, Kulakarni Sripad

doi:10.25135/acg.oc.14.16.10.440

Cited by 5 publications

(3 citation statements)

References 39 publications

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“…Preparation of these compounds is usually done by addition of aldehydes or ketones to two molecules of indole via acid[ 5 , 6 ] or base catalysis. [7] Furthermore, alternative and more sustainable methods have emerged, based on metal‐catalysed[ 8 , 9 ] and metal‐free reactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Bis(3‐indolyl)methanes Mediated by Potassium tert‐Butoxide

et al. 2023

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The indole moiety is an important N-heterocycle found in natural products, and a key structural component of many value-added chemicals including pharmaceuticals. In particular, bis(3-indolyl)methanes (BIMs) are an important subgroup of indoles, composed of two indole units. Herein, we report the development of a simple method to access BIMs derivatives in yields of up to 77 % by exploiting a tBuOK-mediated coupling reaction of indoles and benzyl alcohols.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Bis(3‐indolyl)methanes Mediated by Potassium tert‐Butoxide

et al. 2023

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“…The reaction mechanism is a simple acid-catalyzed Friedel–Crafts bisarylation. The aldehyde is activated by the succinic acid and subsequently undergoes an electrophilic substitution at C-3 and after the loss of water and the addition of the second molecule of indole the corresponding BIM is formed [ 133 ].…”

Section: Reviewmentioning

confidence: 99%

“…This protocol can also be used for the synthesis of tetraindolylmethanes, justifying the drawback of the use of a solvent compared to the rest of the microwave-assisted methodologies [132]. Following Nongkhlaw's study, in 2017, Rao and his research group introduced a new microwave-assisted catalytic protocol, utilizing water once again as the solvent and succinic acid as the catalyst in place of TEBA (Scheme 30) [133]. Succinic acid provided the most promising results, compared to other natu- rally derived organic acids, and the fact that it is a safe, commercially available, non-toxic and biodegradable compound made it an appealing choice.…”

Section: Microwavesmentioning

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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