Synthesis of Aminofuran-Linked Benzimidazoles and Cyanopyrrole-Fused Benzimidazoles by Condition-Based Skeletal Divergence

Hsu, Wei-Shun; Tsai, Min-Huan; Barve, Indrajeet J.; Yellol, Gorakh S.; Sun, Chung‐Ming

doi:10.1021/acscombsci.7b00052

Cited by 4 publications

(5 citation statements)

References 26 publications

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“…The reaction of arylamines 1ab-bc with cyanoacetic acid 6 in variety of conditions gives 2-cyanoacetamide derivatives 3ab-bc (Scheme 3, Table 3). 35,36 Scheme 3…”

Section: Reaction Of Amine With Cyanoacetic Acid In Different Conditionsmentioning

confidence: 99%

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Synthesis and synthetic applications of cyanoacetamides

Abdelhamid¹,

Ghozlan²,

Abdelmoniem³

et al. 2020

Arkivoc

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Approaches for the preparation of cyanoacetamide derivatives as well as the chemical reactivity profiles and structures of these substances are reviewed. The utility of these compounds as precursors is emphasized in the synthesis of five-and six-membered heterocycles and their fused heterocycles. The reported heterocyclic compounds in this review article are classified according to the kind of the heterocyclic systems.

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“…The reaction of arylamines 1ab-bc with cyanoacetic acid 6 in variety of conditions gives 2-cyanoacetamide derivatives 3ab-bc (Scheme 3, Table 3). 35,36 Scheme 3…”

Section: Reaction Of Amine With Cyanoacetic Acid In Different Conditionsmentioning

confidence: 99%

“…Methyl 1-alkyl-(2-cyanometyl)benzimidazole-5-carboxylate 261 was synthesized via boiling of 3eb in 10% trifluoroacetic acid TFA (Scheme 113). 35…”

Section: Scheme 112 32122 1h-benzo[d]imidazolementioning

confidence: 99%

Synthesis and synthetic applications of cyanoacetamides

Abdelhamid¹,

Ghozlan²,

Abdelmoniem³

et al. 2020

Arkivoc

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“…An interesting example of two component condensation reaction of cyanomethylbenzimidazole 75 and α‐bromoketone 76 was reported in two different conditions to produce two different products (Scheme ). This reaction on thermal condition produced 2‐aminofuranyl‐benzimidazoles 78 while under microwave condition 3‐cyano‐benzopyrrolo‐imidazole 77 was obtained …”

Section: Synthesis Of Polycyclic Benzimidazolementioning

confidence: 99%

“…This reaction on thermal condition produced 2-aminofuranyl-benzimidazoles 78 while under microwave condition 3-cyano-benzopyrrolo-imidazole 77 was obtained. [27] An efficient synthesis of medicinally important imidazole connecting benzimidazole polymer conjugates with excellent regioselectivity was developed by using polymer bound amino benzimidazoles 79 with several R-bromoketones 80) in microwave irradiation (Scheme 17). Benzimidazole 79 could be released from the polymer support inside the biological cells at room temperature.…”

Section: Metal Free Approachmentioning

confidence: 99%

Polycyclic Benzimidazole: Synthesis and Photophysical Properties

Manna¹,

Das

Samanta³

2019

ChemistrySelect

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Benzimidazole has tremendous application in medicinal chemistry and material science. The fusion of ring/substitution to benzimidazole nucleus produce polycyclic benzimidazole e. g., pyrido[1,2‐a]benzimidazole, benzimidazo[1,2‐a]quinoline, pyrrolo[1,2‐c]benzimidazolequinones (PBIs) and benzimidazo[2,1‐a]isoquinolines and these are the important synthetic strategies in drug discovery. Benzimidazole analogues have versatile therapeutic properties which encouraged the researchers to develop new therapeutic agents. Hence, the synthetic literature survey towards the polycyclic benzimidazole is paramount important. Due to the beautiful fluorescent properties of fused benzimidazole moiety, they are also used in optoelectronics, optical lasers, and organic luminophores. In addition, this scaffold has broad applications in organometallic catalysis, co‐ordination chemistry, and asymmetric catalysis. Herein, we report a vast synthetic route of benzimidazole embedded polyhetrocycles in the last eight years and their photophysical application in the modern research field.

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“…However, CBD involves generation of structurally diverse scaffolds from the same starting materials via different reaction pathways by varying reaction conditions such as bases, catalysts, solvents. and additives …”

Section: Introductionmentioning

confidence: 99%

Base Controlled Three-Component Regioselective Synthesis of 2-Imino Thiazolines and 2-Thioxoimidazolin-4-ones

et al. 2019

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Base-controlled regioselective synthesis of 2imino thiazolines and 2-thioxoimidazolin-4-ones was achieved to use a one-pot reaction between chiral amino esters, isothiocyanates, and α-bromoketones/alkyl halides. This three-component coupling reaction in acetonitrile provides 2-imino thiazolines, whereas the formation of 2-thioxoimidazolin-4-ones was observed under basic conditions at ambient temperature. The corresponding products were obtained in good to excellent yield with broad substrate scope. Isolation of thiourea and thiohydantoin intermediates disclosed the course of the reaction mechanism.

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Synthesis of Aminofuran-Linked Benzimidazoles and Cyanopyrrole-Fused Benzimidazoles by Condition-Based Skeletal Divergence

Cited by 4 publications

References 26 publications

Synthesis and synthetic applications of cyanoacetamides

Synthesis and synthetic applications of cyanoacetamides

Polycyclic Benzimidazole: Synthesis and Photophysical Properties

Base Controlled Three-Component Regioselective Synthesis of 2-Imino Thiazolines and 2-Thioxoimidazolin-4-ones

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