Ceric ammonium nitrate (CAN): an efficient and eco-friendly catalyst for the one-pot synthesis of alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methanes at room temperature

Brahmachari, Goutam; Banerjee, Bubun

doi:10.1039/c5ra04723d

Cited by 37 publications

(23 citation statements)

References 69 publications

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“…Usually reaction of 6-aminouracil with aldehyde in presence of various catalysts give bis (6-aminouracil-5-yl)methanes. [14] Therefore, in the present reaction there is a possibility of formation of bis-compound. We optimized the condition for the 3component reaction of 1,3-dimethyl-6-aminouracil, benzaldehyde and tetrahydroisoquinoline (THIQ).…”

Section: Resultsmentioning

confidence: 88%

Multi‐Component Reaction of 6‐Aminouracils, Aldehydes and Secondary Amines: Conversion of the Products into Pyrimido[4,5‐d]pyrimidines through C‐H Amination/Cyclization

et al. 2019

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Reaction of 6‐aminouracils with aldehydes and secondary amines catalyzed by acetic acid is reported here. This is in fact a domino aza‐Michael reaction. 6‐Aminouracil reacts first with aldehyde and then amine attacks the newly formed C=C bond, which is established from the mass spectral analysis of the reaction mixture. The products of the reaction are cyclized to pyrimido[4,5‐d]‐pyrimidines via intramolecular α‐C−H functionalization of tertiary amine promoted by I2‐TBHP at room temperature in ethanol solvent. I2 (10 mol %) and TBHP (1.5 eq.) are used for the cyclization reactions. Based on few controlled experiments a tentative radical mechanism is proposed for the cyclization step.

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Section: Resultsmentioning

confidence: 88%

Multi‐Component Reaction of 6‐Aminouracils, Aldehydes and Secondary Amines: Conversion of the Products into Pyrimido[4,5‐d]pyrimidines through C‐H Amination/Cyclization

et al. 2019

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“…The easy recycling is an attractive property of the catalytic system for the environmental protection and economic reasons . Catalyst recycling experiments were explored for the model reaction.…”

Section: Resultsmentioning

confidence: 99%

ZrOCl₂·8H₂O as an efficient and recyclable catalyst for the one‐pot multicomponent synthesis of novel [1,3]oxazino[5,6‐c]quinolin‐5‐one derivatives

Han

Zhou

2019

Applied Organom Chemis

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A simple, efficient and eco‐friendly procedure has been developed using ZrOCl2·8H2O as catalyst for the synthesis of novel [1,3]oxazino[5,6‐c]quinolin‐5‐one derivatives in aqueous ethanol at room temperature. The present methodology offers several advantages such as operational simplicity, use of ZrOCl2·8H2O as a green, non‐toxic, inexpensive and reusable catalyst, reusability of reaction media, high yields, mild and environmentally benign reaction conditions.

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“…Moreover, reusability of the reaction media is an added advantage to this protocol. [192][193][194][195] Brahmachari and his group reported a straightforward and efficient pseudo three-component onepot synthesis of a series of substituted bis(6-aminouracil-5-yl)methanes 86 in good yields using either ceric ammonium nitrate (CAN) 196 or sulfamic acid 197 as commercially available, inexpensive and eco-friendly catalyst from the reaction of 6-aminouracils (85) and diverse aldehydes (1) in aqueous ethanol at room temperature (Scheme 30). Scheme 28.…”

Section: Scheme 27 Synthesis Of Substituted Alkenes 76 Via Knoevenagmentioning

confidence: 99%

Design for carbon–carbon bond forming reactions under ambient conditions

Brahmachari

2016

RSC Adv.

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Carbon-carbon (C-C) bond forms the 'backbone' of nearly every organic molecule, and lies at the heart of the chemical sciences! This transformation has always been one of the most useful and fundamental reactions in the development of organic chemistry. Currently, the concept of 'green chemistry' is globally acclaimed and has already advanced quite significantly to come out as a distinct branch of chemical sciences. Among the principles of 'green chemistry', one principle is dedicated to "design of energy efficiency" -that is to develop synthetic strategies that require less/minimum amount of energy to carry out a specific reaction with optimum productivity. And the most effective way-out to save energy is to develop strategies/protocols that are capable enough to carry out the transformations at ambient temperature and pressure! As part of on-going developments on green synthetic strategies, designing for reactions under ambient conditions coupled with other green aspects is, thus, an area of current choice. This review is aimed to offer an up-to-date development on the design of carbon-carbon bond forming protocols to access a wide variety of organic molecules of topical significance under ambient conditions. The account highlights on the brilliant applications of reaction conditions such as the use of solvents or no solvent, catalysts or no catalyst, and the use of green tools like ball-milling, ultrasonication and visible light in achieving the goal! Design for Carbon Carbon Frameworks at Ambient ConditionsN Me Me Me O O COOH Br Br (Graphic for TOC)

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Ceric ammonium nitrate (CAN): an efficient and eco-friendly catalyst for the one-pot synthesis of alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methanes at room temperature

Abstract: Ceric ammonium nitrate (CAN)-catalyzed one-pot synthesis of alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methane scaffolds (3a–3u) has been developed via a pseudo three-component reaction in aqueous ethanol at room temperature.

Cited by 37 publications

References 69 publications

Multi‐Component Reaction of 6‐Aminouracils, Aldehydes and Secondary Amines: Conversion of the Products into Pyrimido[4,5‐d]pyrimidines through C‐H Amination/Cyclization

Multi‐Component Reaction of 6‐Aminouracils, Aldehydes and Secondary Amines: Conversion of the Products into Pyrimido[4,5‐d]pyrimidines through C‐H Amination/Cyclization

ZrOCl₂·8H₂O as an efficient and recyclable catalyst for the one‐pot multicomponent synthesis of novel [1,3]oxazino[5,6‐c]quinolin‐5‐one derivatives

Design for carbon–carbon bond forming reactions under ambient conditions

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Ceric ammonium nitrate (CAN): an efficient and eco-friendly catalyst for the one-pot synthesis of alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methanes at room temperature

Abstract: Ceric ammonium nitrate (CAN)-catalyzed one-pot synthesis of alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methane scaffolds (3a–3u) has been developed via a pseudo three-component reaction in aqueous ethanol at room temperature.

Cited by 37 publications

References 69 publications

Multi‐Component Reaction of 6‐Aminouracils, Aldehydes and Secondary Amines: Conversion of the Products into Pyrimido[4,5‐d]pyrimidines through C‐H Amination/Cyclization

Multi‐Component Reaction of 6‐Aminouracils, Aldehydes and Secondary Amines: Conversion of the Products into Pyrimido[4,5‐d]pyrimidines through C‐H Amination/Cyclization

ZrOCl2·8H2O as an efficient and recyclable catalyst for the one‐pot multicomponent synthesis of novel [1,3]oxazino[5,6‐c]quinolin‐5‐one derivatives

Design for carbon–carbon bond forming reactions under ambient conditions

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Product

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ZrOCl₂·8H₂O as an efficient and recyclable catalyst for the one‐pot multicomponent synthesis of novel [1,3]oxazino[5,6‐c]quinolin‐5‐one derivatives