Catalyst-free synthesis of novel 1,5-benzodiazepines and 3,4-dihydroquinoxalines using isocyanide-based one-pot, three- and four-component reactions

Mohlala, Reagan Lehlogonolo; Coyanis, E. Mabel; Fernandes, Manuel A.; Bode, Moira L.

doi:10.1039/d1ra04444c

Cited by 14 publications

(5 citation statements)

References 42 publications

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“…MCRs have been used for more than a century; yet it is still unclear who made the first discovery and first publication of an MCR, however, the Strecker multicomponent reaction [84 ] (S-3CR) was described in 1850, followed by the Hantzsch [85 ] dihydropyridine (DHP) synthesis reported in 1882. To date, MCRs are considered an advantageous approach because of their ability to rapidly generate molecular diversity and structural complexity of interest for different applications [86,87].…”

Section: Discussionmentioning

confidence: 99%

Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

Mohlala¹,

Rashamuse²,

Coyanis³

2023

Preprint

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Multicomponent reactions (MCRs) have been used for more than a century; since their discovery in 1850 by Strecker. To date, MCRs route is regarded as a beneficial strategy due to its capacity to quickly produce molecular diversity and structural complexity of interest for a variety of applications. Despite having famous MRCs such as the Ugi, Passerini, Biginelli, and Hantzsch, this re-view portrays the importance of MCRs in the synthesis of desired products towards applications such as medicinal purposes, sustainable chemistry, and polymerisation. MCRs provide ad-vantages such as reducing the number of sequential multiple reactions to one step, atom economy, recyclable catalysts, mild conditions, preventing waste and reduce solvent use.

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Section: Discussionmentioning

confidence: 99%

Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

Mohlala¹,

Rashamuse²,

Coyanis³

2023

Preprint

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“…[106] But the reaction of isocyanide with 1,2-phenylenediamine using two equivalents of acetone in the presence of ammonium chloride as catalyst provided benzodiazepine-2-carboxamides (Yield~60-72 %) (Scheme 37) [127] Mohlala and coworkers used isocyanide-based reaction to synthesize 3,4-dihydroquinoxalines. [128] involving the reaction ofbenzimidazolone containing electron-withdrawing group with acetone and isocyanide. The reaction is supposed to proceed with the generation of imine intermediate in the first step with the involvement of one of the nitrogen atoms of benzimidazolone in the reaction with acetone.…”

Section: Synthesis Of 34-dihydroquinoxalines and 15-benzodiazepinesmentioning

confidence: 99%

“…Mohlala and coworkers used isocyanide‐based reaction to synthesize 3,4‐dihydroquinoxalines [128] . involving the reaction ofbenzimidazolone containing electron‐withdrawing group with acetone and isocyanide.…”

Section: Synthesis Of Quinoxalinesmentioning

confidence: 99%

Advances in Isocyanide‐Based Multicomponent Synthesis of Quinoxaline Scaffolds

Agarwal,

Verma,

Pathak

et al. 2023

ChemistrySelect

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The present review article includes recent advances in the synthesis of structurally and functionally diversified quinoxalines‐drug‐like small molecules with molecular complexity. We have extended our efforts to include the research work concerning the isocyanide‐based multicomponent reactions. The synthetic methods included in the present review article will provide an access for a diverse range of natural product mimetic scaffolds with the use of isocyanide‐.based combinatorial synthesis. These isocyanide based reactions will be significant for the synthesis of complex bioactive natural products and potential synthetic pharmaceuticals. The present review will contribute considerably to the organic syntheses and particularly drug discovery research including pharmaceutical and medicinal chemistry. Academically, the present review article will be interesting for the researchers engaged in design and development of isocyanide‐based organic transformations. Moreover, we hope that the isocyanide‐based multicomponent reactions will find major applications in industrially significant organic transformations and to develop new synthetic routes to facilitate the incorporation of heterocyclic substructures into pharmaceutically active molecules.

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“…Explicit confirmation for the structures of 13a, 13b, 13d and 8 was obtained from single-crystal X-ray analysis (Figure 3). These compounds were prepared as part of our ongoing efforts towards identifying novel heterocycles with biological activity [46][47][48]. Compounds showing cytotoxicity values of >200 µM in MT-4 cells were evaluated for activity in an HIV assay (see Supplementary Materials).…”

Section: Synthesis Of 5h-thiazolo[32-a]pyrimidine-7-carboxylates Using Two-component and Three-component Reactionsmentioning

confidence: 99%

“…For mass spectrometry (LC-MS/MS), highresolution mass spectra were obtained. Fourier infrared spectra (FTIR) were recorded by These compounds were prepared as part of our ongoing efforts towards identifying novel heterocycles with biological activity [46][47][48]. Compounds showing cytotoxicity values of >200 µM in MT-4 cells were evaluated for activity in an HIV assay (see Supplementary Materials).…”

Section: General Informationmentioning

confidence: 99%

Synthesis of 6-Membered-Ring Fused Thiazine-Dicarboxylates and Thiazole-Pyrimidines via One-Pot Three-Component Reactions

et al. 2021

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A facile and efficient one-pot three-component reaction method for the synthesis of thiazine-dicarboxylates is reported. Reaction of an isocyanide and dialkyl acetylenedicarboxylate with 2-amino-4H-1,3-thiazin-4-one derivatives containing both an acidic proton and an internal nucleophile gave the products in good yields of 76–85%. The reactivity of dialkyl acetylenedicarboxylates was further tested in the synthesis of thiazole-pyrimidines where a two-component reaction of 2-aminothiazole with dialkyl acetylenedicarboxylates was successfully converted to a more efficient three-component reaction of a thiourea, α-haloketone and dialkyl acetylenedicarboxylate (DMAD/DEtAD) to give thiazole-pyrimidines in good yields of 70–91%.

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Catalyst-free synthesis of novel 1,5-benzodiazepines and 3,4-dihydroquinoxalines using isocyanide-based one-pot, three- and four-component reactions

Abstract: Reaction of benzimidazole derivatives with an isocyanide and acetone led to tricyclic benzodiazepine derivatives or dihydroquinoxalines depending on the nature of the substituents R1 and R2.

Cited by 14 publications

References 42 publications

Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

Advances in Isocyanide‐Based Multicomponent Synthesis of Quinoxaline Scaffolds

Synthesis of 6-Membered-Ring Fused Thiazine-Dicarboxylates and Thiazole-Pyrimidines via One-Pot Three-Component Reactions

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