ZnBr<sub>2</sub>Mediated C−N Bond Formation using Cinnamyl Alcohol and 2‐Amino Pyridines

Panigrahi, Ahwan; Sherikar, Mahadev Sharanappa; Prabhu, Kandikere Ramaiah

doi:10.1002/ejoc.202100463

Cited by 3 publications

(1 citation statement)

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“…10 In our continuing investigations of this system, we herein report the N -benzylation of poor nucleophilic 2-aminopyridine substrates via catalytic direct S N 1-type amination of benzhydrols in water (Scheme 1C). 11 Screening and optimization of catalysts revealed that a combination of HAuCl 4 ·xH 2 O (x = 3 or 4) catalyst and TPPMS ligand showed good catalytic activity for the N -benzylation in water. Notably, since amine nucleophiles having reducible sensitive functionalities such as a nitro group could be utilized without decomposition, this method would become an alternative borrowing hydrogen reaction.…”

Section: Introductionmentioning

confidence: 99%

Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(iii)/TPPMS catalyst system in water

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(iii)/TPPMS catalyst system in water

et al. 2022

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PhI(OAc)₂/I₂‐Mediated Decarboxylative C₄‐Amination of Coumarin‐3‐Carboxylic Acids via C_sp2−H Dehydrogenative C−N Cross‐Coupling under Ambient Conditions

Bhowmick

Brahmachari

2023

Eur J Org Chem

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An efficient and straightforward protocol for accessing a new series of functionalized 4-aminocoumarins from PIDA/I 2 -mediated decarboxylative C 4 -amination of coumarin-3-carboxylic acids via direct C sp2 À H dehydrogenative CÀ N cross-coupling with secondary amines under ambient conditions has been accomplished. The notable advantages of this protocol are the tolerance of diverse functional groups, mild reaction conditions at ambient temperature, moderate to good yields, short reaction times (in minutes), high regioselectivity, gram-scale applicability, and eco-friendliness. This is the first report of decarboxylative C sp2 À H cross-dehydrogenative CÀ N coupling of coumarin-3-carboxylic acids for synthesizing 4-aminocoumarins.

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Energy-efficient Approach to Multicomponent Reaction for the Synthesis of Therapeutically Relevant Heterocycles

Roy,

Kumar,

Ansari

et al. 2023

COC

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Multi-component reactions have been used as an important synthetic strategy for the synthesis of diverse varieties of therapeutically useful heterocyclic scaffolds. High atom economy, one-pot reaction, and involvement of synthetically simple steps are some of the interesting features that make MCRs greener compared to conventional methods. The development of environmentally benign and eco-friendly synthetic methods has been a very demanding area of research in the past few decades. In particular, the development of energyefficient methods has attracted the attention of the research community due to heavy dependence on nonrenewable energy resources, which is depleting fast. Therefore, the present review has highlighted the multicomponent reactions developed under the energy efficient protocol, which mainly include the reactions developed under the microwave, ultra-sonication, mechano-chemical, and photochemical reaction conditions for the synthesis of therapeutically relevant heterocycles.

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ZnBr₂Mediated C−N Bond Formation using Cinnamyl Alcohol and 2‐Amino Pyridines

Cited by 3 publications

References 29 publications

Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(iii)/TPPMS catalyst system in water

Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(iii)/TPPMS catalyst system in water

PhI(OAc)₂/I₂‐Mediated Decarboxylative C₄‐Amination of Coumarin‐3‐Carboxylic Acids via C_sp2−H Dehydrogenative C−N Cross‐Coupling under Ambient Conditions

Energy-efficient Approach to Multicomponent Reaction for the Synthesis of Therapeutically Relevant Heterocycles

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ZnBr2Mediated C−N Bond Formation using Cinnamyl Alcohol and 2‐Amino Pyridines

Cited by 3 publications

References 29 publications

Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(iii)/TPPMS catalyst system in water

Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(iii)/TPPMS catalyst system in water

PhI(OAc)2/I2‐Mediated Decarboxylative C4‐Amination of Coumarin‐3‐Carboxylic Acids via Csp2−H Dehydrogenative C−N Cross‐Coupling under Ambient Conditions

Energy-efficient Approach to Multicomponent Reaction for the Synthesis of Therapeutically Relevant Heterocycles

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ZnBr₂Mediated C−N Bond Formation using Cinnamyl Alcohol and 2‐Amino Pyridines

PhI(OAc)₂/I₂‐Mediated Decarboxylative C₄‐Amination of Coumarin‐3‐Carboxylic Acids via C_sp2−H Dehydrogenative C−N Cross‐Coupling under Ambient Conditions