Divergent construction of 3-(indol-2-yl)succinimide/maleimide and fused benzodiazepine skeletons from 2-(1<i>H</i>-indol-1-yl)anilines and maleimides

Ma, Chunhua; Wang, Yue; Chen, Guang; Li, Jingyi; Jiang, Yuqin; Zhang, Xinying; Fan, Xuesen

doi:10.1039/d2qo00779g

Cited by 11 publications

(2 citation statements)

References 51 publications

(16 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…While previous studies have explored reactions between maleimide and anilines, [41][42][43][44][45][46] the chemistry of maleimide with hydrazine, which bears similarities to aniline but remains relatively unexplored, presents an interesting opportunity. In the present study, We have developed a methodology using the VLCF approach to obtain isoniazid and maleimide derivatives.…”

Section: Resultsmentioning

confidence: 99%

Visible Light‐Promoted Catalyst‐Free (VLCF) Scalable Synthesis of Novel Derivatives of Isoniazid and Maleimide

Iqbal,

Hussain,

Singh

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

We have developed a Visible Light Promoted Catalyst‐Free (VLCF) approach to synthesize novel conjugates of Isoniazid and Maleimide. This method involves the formation of an electron donor‐acceptor (EDA) complex between isoniazid and maleimide the photochemical activity of this complex drives the transformation. We successfully synthesized Isoniazid‐Maleimide derivatives (3a–d) at gram scale under visible light irradiation without an additional photo catalyst and without chromatographic purification resulting in excellent yields in a recyclable green solvent. Molecular docking was employed to predict the in silico anti‐tubercular activity and binding modes at the active site of enoyl‐ACP reductase, InhA. The newly synthesized compounds (3a–d) exhibited high binding affinity compared to Isoniazid and Isoniazid‐NAD adduct, indicating their potential for more effective anti‐tubercular activity. ADME analysis revealed favourable physicochemical properties, lipophilicity, water solubility, pharmacokinetics, and drug‐likeness for compound 3a, positioning it as a promising candidate for further drug discovery and development.

show abstract

Section: Resultsmentioning

confidence: 99%

Visible Light‐Promoted Catalyst‐Free (VLCF) Scalable Synthesis of Novel Derivatives of Isoniazid and Maleimide

Iqbal,

Hussain,

Singh

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…The primary challenges emanate from its intrinsic reactivity, such as its strong coordination with a metal catalyst leading to catalyst deactivation, substrate and product decomposition through overoxidation, and its innate nucleophilic reactivity, which results in the formation of undesired byproducts (Scheme a) . In fact, because of the nucleophilic reaction profile, the majority of the free amine-directed Ru(II)-catalyzed C–H activation and functionalization reactions have been documented in the form of annulation reactions where the amine functionality is integrated into a ring framework. − Of note, heretofore, free amine-directed Ru(II)-catalyzed C–H arylation has not been reported (Scheme a).…”

mentioning

confidence: 99%

Free Amine-Directed Redox Neutral Ruthenium(II) Catalysis toward Regioselective Synthesis of Heterobiaryls

Ghosh,

Koner,

Kunhiraman

et al. 2024

Org. Lett.

View full text Add to dashboard Cite

A regioselective coupling of ortho-heteroaryl anilines and 7-oxabenzonorbornadienes has been developed by leveraging free amine-directed redox-neutral Ru(II) catalysis. This protocol facilitates formal C-2 arylation of the indole moiety under mild conditions to offer valuable heterobiaryls in high yields. The reaction displays a broad substrate generality and scalability and retains efficacy in the presence of diverse pharmacophore scaffolds. Moreover, products bearing a free amine group were successfully employed in Mg(NTf 2 ) 2 -catalyzed double Michael addition cascade, which led to the synthesis of intricate indole-and pyrrole-fused azaheterocycles.

show abstract

Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles

Zhao,

Pi,

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

Herein, a Rh‐catalyzed redox C7‐spiroannulation reaction of N‐benzo[d]imidazole indolines with maleimides has been reported, chemo‐ and regio‐ selectively providing a series of N‐benzo[d]imidazole indoline fused azaspirocycles in up to 92% yield. The synthetic utility is demonstrated by the synthesis of highly functionalized nitrogen‐containing spiropolycyclic skeletons, which could be extended to maleic esters and acrylates. The products could be purified through simple filtration. The recyclable Rh catalyst and scale‐up synthesis with as low as 0.5 mol% catalyst loading makes this protocol potential application in industrial. Moreover, the efficient post‐modification of pharmaceutical molecules demonstrates its practicability.

show abstract

Divergent construction of 3-(indol-2-yl)succinimide/maleimide and fused benzodiazepine skeletons from 2-(1H-indol-1-yl)anilines and maleimides

Cited by 11 publications

References 51 publications

Visible Light‐Promoted Catalyst‐Free (VLCF) Scalable Synthesis of Novel Derivatives of Isoniazid and Maleimide

Visible Light‐Promoted Catalyst‐Free (VLCF) Scalable Synthesis of Novel Derivatives of Isoniazid and Maleimide

Free Amine-Directed Redox Neutral Ruthenium(II) Catalysis toward Regioselective Synthesis of Heterobiaryls

Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles

Contact Info

Product

Resources

About