Visible-light-mediated one-pot efficient synthesis of 1-aryl-1H,3H-thiazolo[3,4-a]benzimidazoles: a metal-free photochemical approach in aqueous ethanol

Nazeef, Mohd; Shivhare, Km Neha; Ali, Shabir; Ansari, Saif; Siddiqui, I. R.

doi:10.1007/s11030-020-10145-8

Cited by 7 publications

(3 citation statements)

References 36 publications

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“…Siddiqui and co‐workers demonstrated an efficient photochemical synthesis of 1‐aryl‐1 H ,3 H ‐thiazolo[3,4‐ a ]benzimidazoles 663 using1,2‐phenylenediamines 628 , aromaticaldehydes 1 and 2‐mercaptoacetic acid in aqueous ethanol (Scheme 141). [159] In the Initial step, the nucleophilic addition reaction between 1,2‐phenylenediamine 628 and benzaldehyde 1 followed by dehydration formed intermediate 664 which then reacts with 2‐mercaptoacetic acid formed intermediate 665 . Next, intermediate 665 was irradiated in the presence of visible light generate produced α‐thiol‐substituted acyl radical which followed by radicals coupling and cyclization formed intermediate 666 .…”

Section: Miscellaneous Reactionmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, the use of transition metal catalysts or additives in MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest in transition metal‐free MCRs for the synthesis of N‐heterocyclic compounds. This review provides a comprehensive and concise overview of the recent advancements in transition metal‐free MCRs for the synthesis of valuable N‐heterocycles over the past five years. The review is systematically organized, categorizing the discussed MCRs based on the size of the heterocyclic ring and the number of nitrogen atoms. Only MCRs that result in the formation of heterocyclic rings containing at least one nitrogen atom are included, while the derivatization of N‐heterocycles using transition metal‐free MCRs falls outside the scope of this review. By highlighting the recent developments in this field, this review aims to showcase the potential and significance of transition metal‐free MCRs as sustainable and efficient strategies for accessing N‐heterocyclic compounds. The elimination of transition metals not only simplifies the reaction conditions but also contributes to greener and more environmentally friendly synthetic approaches. This review serves as a valuable resource for researchers interested in the design and application of transition metal‐free MCRs in the synthesis of nitrogen‐containing heterocycles.

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Section: Miscellaneous Reactionmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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“…A comparative study of proposed protocol with the previously reported methods is depicted below (Scheme 1). Thus, in continuation of our research program for the synthesis of biologically relevant heterocyclic compounds via green methods [26], we herein reported an efficient and ecocompatible one-pot synthetic strategy for the synthesis of 4-oxo-tetrahydroindole derivatives in the presence of visible light under aqueous ethanol at room temperature. Binary solution of ethanol-water (1:1) was found more suitable solvent system owing to its green credential [27].…”

Section: Introductionmentioning

confidence: 99%

A metal‐free visible light promoted three‐component facile synthesis of 4‐oxo‐tetrahydroindoles in ethanol–water

Ansari

Nazeef

Ali

et al. 2020

Journal of Heterocyclic Chem

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A mild and efficient visible light–mediated one‐pot multicomponent tandem approach to construct 4‐oxo‐tetrahydroindoles in ethanol–water medium at room temperature has been described. The characteristics of reported methodology are the utilization of visible light, an ideal source of energy to generate CC and CN bonds from commercially available substrates namely dimedone, phenacyl bromides, and amines. The presented protocol is highly compatible for developing 4‐oxo‐tetrahydroindole derivatives with improved selectivity and high yields. Moreover, metal‐free synthesis, environmental friendly solvent, easy workup process, high atom economy, cost‐effectiveness, short reaction time, and broad substratescope are the major advantages of reported protocol.

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“…In continuation of our ongoing research program on the development of green synthetic routes to biologically significant heterocyclic compounds, [41][42][43][44] we herein report a new and efficient, operationally simple, catalyst free, glycerol promoted one-pot synthesis of benzo[a]chromeno[2,3-c]phenazines (Scheme 1). (Table 1, Entry 1).…”

Section: Introductionmentioning

confidence: 99%

Catalyst Free, Multicomponent Green Approach to Benzo[a]chromeno[2,3‐c]phenazines Using Glycerol as a Recyclable and Biodegradable Promoting Medium

et al. 2020

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A series of benzo[a]chromeno[2,3‐c]phenazine derivatives were synthesized through an efficient one‐pot, multicomponent eco‐friendly reaction of 2‐hydroxynaphthalene‐1,4‐dione, o‐phenylenediamines, cyclic 1,3‐dicarbonyl compounds and aromatic aldehydes, promoted by glycerol. To the best of our knowledge this is the first catalyst free protocol for synthesis of this important scaffold having potential applications in medicinal and materials chemistry. Other important attributes of the present method are the use of glycerol as a bio‐renewable and biodegradable reaction medium‐cum‐promoter, use of readily available substrates, mild reaction conditions, operational simplicity, broad substrate scope, short reaction time, easy workup, and high yields and atom efficiency, which makes the disclosed protocol a superior alternative to existing methods.

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Visible-light-mediated one-pot efficient synthesis of 1-aryl-1H,3H-thiazolo[3,4-a]benzimidazoles: a metal-free photochemical approach in aqueous ethanol

Cited by 7 publications

References 36 publications

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

A metal‐free visible light promoted three‐component facile synthesis of 4‐oxo‐tetrahydroindoles in ethanol–water

Catalyst Free, Multicomponent Green Approach to Benzo[a]chromeno[2,3‐c]phenazines Using Glycerol as a Recyclable and Biodegradable Promoting Medium

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