Accessing Polysubstituted Quinazolines via Nickel Catalyzed Acceptorless Dehydrogenative Coupling

Parua, Seuli; Sikari, Rina; Sinha, Suman; Chakraborty, Gargi; Mondal, Rakesh; Paul, Nanda D.

doi:10.1021/acs.joc.8b01479

Cited by 108 publications

(33 citation statements)

References 72 publications

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“…These quinazolines have been proposed to be employed as a high fluorescent probe (Patel and Patel, 2019). Parua et al developed nickel [Ni(MeTAA)]-catalyzed approach for the formation of quinazoline derivatives 126 from acceptor-less dehydrogenative coupling of 2-aminobenzylamines 22 with benzyl alcohols 125 and 2-aminobenzylalcohols 88 with benzonitriles 127 in the presence of potassium tertbutoxide in xylene at 100 • C for 24 h (Parua et al, 2018). The environmentally benign methodology, easy to prepare nickel catalyst, and broad substrate scope made this methodology beneficial (Scheme 33).…”

Section: Nickel-mediated Catalytic Systemsmentioning

confidence: 99%

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

Faisal

Saeed

2021

Front. Chem.

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In medicinal chemistry, one of the most significant heterocyclic compounds are quinazolines, possessing broad range of biological properties such as anti-bacterial, anti-fungal, anti-HIV, anti-cancer, anti-inflammatory, and analgesic potencies. Owing to its numerous potential applications, in the past two decades, there is an increase in the importance of designing novel quinazolines, exploring promising routes to synthesize quinazolines, investigating different properties of quinazolines, and seeking for potential applications of quinazolines. The present review article describes synthesis of quinazolines via eco-friendly, mild, atom-efficient, multi-component synthetic strategies reported in the literature. The discussion is divided into different parts as per the key methods involved in the formation of quinazoline skeletons, aiming to provide readers an effective methodology to a better understanding. Consideration has been taken to cover the most recent references. Expectedly, the review will be advantageous in future research for synthesizing quinazolines and developing more promising synthetic approaches.

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Section: Nickel-mediated Catalytic Systemsmentioning

confidence: 99%

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

Faisal

Saeed

2021

Front. Chem.

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“…Drug likeness: There are many approaches around that assess a compound's drug likeness partially based on topological descriptors, fingerprints of MDL structure keys or other properties as cLogP and molecular weights. Overall drug score: The drug score combines drug likeness, cLogP, logS, molecular weight and toxicity risks in one handy value than may be used to judge the compound's overall potential to qualify for a drug [54][55][56][57][58][59][60].…”

Section: Osiris Property Explorer and Drug Relevant Properties Predictionmentioning

confidence: 99%

Benzimidazole Molecule Hybrid With Oxadiazole Ring as Antiproliferative Agents: In-Silico Analysis, Synthesis and Biological Evaluation

Rashid

2021

J. Chil. Chem. Soc.

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A new series of benzimidazole molecules hyride with oxadiazole ring were design with an intention to search new antiproliferative lead compound. In-Silico toxicity of lead compound was also performed by using T.E.S.T software tool, a program from US Environmental Protection Agency. Drug like properties and bioactivity score for drug targets of designed compounds were calculated by molinspiration tool and obtained result found to obey Lipinski's rule that indicates the compound are orally active molecules. Osiris property explorer was used for the prediction of drug relevant properties and toxicity of synthetic compounds. Pre ADMET server was also used to estimate ADME properties of synthetic compounds. Antiproliferative activities of compounds were investigated at the National Cancer Institute (NCI) against NCI 60 cell line panel, results showed good to notable anticancer activity. So that, these new hybrids compounds could serve as potential template to become leads in near future for the discovery and development of new effect orally drugs molecules. Two compounds, 4c[1-(1H-benzo[d]imidazol-2-yl)-3-(5-((4-methylpiperazin-1-yl)methyl)-1,3,4 -oxadiazol-2-yl) propan-1-one] and 4k[3-((5-(3-(1H-benzo[d]imidazol-2-yl)-3oxopropyl)-1, 3, 4-oxadiazol-2-yl) methyl)-5-methylpyrimidine-2,4(1H, 3H)-dione] were exhibited highest drug score and emerged as lead compounds and motivates for further development of more effective and safer compounds.

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“…Using the same Ni‐catalyst [Ni(MeTAA)], Nanda and co‐workers demonstrated two different acceptorless dehydrogenative methods to access quinazolines (Scheme ) . In the presence of base ( t BuOK) and Ni‐catalyst successfully promoted the coupling of 2‐aminobenzyl alcohol coupled with benzonitrile or 2‐amino benzylamine coupled with benzyl alcohol.…”

Section: Nickel‐catalyzed Dehydrogenative Bond Formationsmentioning

confidence: 99%

Nickel‐Catalyzed Dehydrogenative Couplings

2019

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In last decade, nickel-catalyzed organic reactions made tremendous progress due to their distinctive redox character. It has unfolded many contemporary synthetic transformations namely cross-coupling, carbon-carbon bond cleavage and directed CÀ H functionalization to achieve the targeted medicinal organic molecules in a straightforward manner. Beyond these well documented approaches, dehydrogenative coupling a challenging bond forming strategy by expelling hydrogen from unfunctionalized coupling partners is less explored. In accord with this, nickel-catalyst has been studied to perform different class of dehydrogenative coupling between easily accessible substrates. Nickel catalyzed processes for the construction of carbon-carbon, carbon-heteroatom and heteroatom-heteroatom bonds by dehydrogenation are discussed herein in a sustainable manner.[a] Dr.

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Accessing Polysubstituted Quinazolines via Nickel Catalyzed Acceptorless Dehydrogenative Coupling

Cited by 108 publications

References 72 publications

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

Benzimidazole Molecule Hybrid With Oxadiazole Ring as Antiproliferative Agents: In-Silico Analysis, Synthesis and Biological Evaluation

Nickel‐Catalyzed Dehydrogenative Couplings

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