Cu–benzotriazole-catalyzed electrophilic cyclization of N-arylimines: a methodical tandem approach to O-protected-4hydroxyquinazolines-

Battula, Satyanarayana; Vishwakarma, Ram A.; Ahmed, Qazi Naveed

doi:10.1039/c4ra07377k

Cited by 20 publications

(8 citation statements)

References 33 publications

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“…A similar intermediate has been supported by a previous theoretical study on the copper‐catalyzed synthesis of azoles . This hypothesis found support from related literature on Cu‐benzotriazole‐catalyzed electrophilic cyclization of N ‐arylamines, as well as Cu‐catalyzed synthesis of isoquinoline derivatives or other heteroarenes …”

Section: Resultssupporting

confidence: 81%

A Copper‐Benzotriazole‐Based Coordination Polymer Catalyzes the Efficient One‐Pot Synthesis of (N′‐Substituted)‐hydrazo‐4‐aryl‐1,4‐dihydropyridines from Azines

et al. 2016

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As eries of new (N'-substituted)-hydrazo-4-aryl-1,4-dihydropyridinesw as successfully synthesized via af acile one-pot catalytic pathwayu tilizing azines andp ropiolate esters as starting materialsa nd ao ne-dimensional copper benzotriazole-based coordination polymer as catalyst. In the absence of catalyst, the corresponding 5-substituted 4,5-dihydropyra-zoles were formed in moderate to high yields.F inetuning of the catalysts allowed us to gain more insights regarding the plausible reactionmechanism.Scheme2.Plausible mechanism for the synthesis of the (N'substituted)-hydrazo-4-aryl-1,4-dihydropyridines throught he hydrazine and propiolate Cu-catalyzed coupling.

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Section: Resultssupporting

confidence: 81%

A Copper‐Benzotriazole‐Based Coordination Polymer Catalyzes the Efficient One‐Pot Synthesis of (N′‐Substituted)‐hydrazo‐4‐aryl‐1,4‐dihydropyridines from Azines

et al. 2016

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“…The process is practical for production of numerous functionalized quinazolines 72 with high functional group tolerance as well as a broad spectrum of substrates. On the same note, Vishwakarma et al demonstrated Cu-catalyzed effective approach for forming o -protected-4-hydroxyquinazolines 75 from 2-aminobenzonitriles 73 , substituted aldehydes 68 , and substituted alcohols 74 through the development of an N -functionalized bicyclic precursor, followed by nucleophilic attack of the alkoxy moiety (Battula et al, 2014 ). The synthesis was sufficiently explored with a wide spectrum of substituted 2-aminobenzonitriles and aldehydes led to respective quinazolines 75 in moderate to excellent isolated yields (41–88%) ( Scheme 22D ).…”

Section: Transition Metal-catalyzed Methodologiesmentioning

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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“…The reaction proceeded via the treatment of 2-aminobenzonitriles 73 with aldehydes 9 in the presence of Cu(I)-benzotriazole, K 2 CO 3 , and 4 Å molecular sieves in alcohol at 90°C, providing quinazolines 74 in 72%–86% yields ( Scheme 10B ). ( Battula et al, 2014 ) Use of Cu in catalytic amounts is the benefit of this protocol despite long reaction time and relatively high temperature. In addition, this is the first approach for synthesis of o -protected-4-hydroxyquinazolines 75 through a monocyclic system via a bicyclic intermediate.…”

Section: First-row Transition Metal Catalystsmentioning

confidence: 99%

Transition-metal-catalyzed synthesis of quinazolines: A review

2023

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Quinazolines are a class of nitrogen-containing heterocyclic compounds with broad-spectrum of pharmacological activities. Transition-metal-catalyzed reactions have emerged as reliable and indispensable tools for the synthesis of pharmaceuticals. These reactions provide new entries into pharmaceutical ingredients of continuously increasing complexity, and catalysis with these metals has streamlined the synthesis of several marketed drugs. The last few decades have witnessed a tremendous outburst of transition-metal-catalyzed reactions for the construction of quinazoline scaffolds. In this review, the progress achieved in the synthesis of quinazolines under transition metal-catalyzed conditions are summarized and reports from 2010 to date are covered. This is presented along with the mechanistic insights of each representative methodology. The advantages, limitations, and future perspectives of synthesis of quinazolines through such reactions are also discussed.

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Cu–benzotriazole-catalyzed electrophilic cyclization of N-arylimines: a methodical tandem approach to O-protected-4hydroxyquinazolines-

Abstract: A remarkably efficient approach to O-protected-4-hydroxyquinazolines has been developed via the copper-benzotriazole (Cu-BtH)catalyzed intramolecular electrophilic cyclization of N-arylimines, achieved through the reaction of 2-aminobenzonitriles and various aldehydes.

Cited by 20 publications

References 33 publications

A Copper‐Benzotriazole‐Based Coordination Polymer Catalyzes the Efficient One‐Pot Synthesis of (N′‐Substituted)‐hydrazo‐4‐aryl‐1,4‐dihydropyridines from Azines

A Copper‐Benzotriazole‐Based Coordination Polymer Catalyzes the Efficient One‐Pot Synthesis of (N′‐Substituted)‐hydrazo‐4‐aryl‐1,4‐dihydropyridines from Azines

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

Transition-metal-catalyzed synthesis of quinazolines: A review

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