LiClO4-catalyzed three-component-coupling reactions: a facile synthesis of homoallylic amines

Yadav, J. S.; Reddy, B. V. Subba; Reddy, Padi Pratap; Rao, M. Shesha

doi:10.1016/s0040-4039(02)01324-2

Cited by 32 publications

(5 citation statements)

References 17 publications

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“…Lewis acid catalysts often get decomposed or deactivated after the reaction and more than stoichiometric amount of the catalyst is required to complete the reaction. On the other hand, LPDE does not get decomposed or deactivated even after the reaction with basic amino compounds and effectively proceeds towards the completion of the reaction . As compared to other common Lewis acid catalysts based on main group metals (such as aluminium, boron, tin, titanium, iron etc.)…”

Section: ‐ Optimization Of Catalytic System For Pyrazole Synthesis[a]mentioning

confidence: 99%

An Unexplored Lewis Acidic Catalytic System for Synthesis of Pyrazole and its Biaryls Derivatives with Antimicrobial Activities through Cycloaddition‐Iodination‐Suzuki Reaction

et al. 2019

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Here an environmentally friendly process has been developed for the synthesis of pyrazole and its derivatives through cycloaddition‐iodination‐Suzuki type reaction by the use of lithium perchlorate as a Lewis acid catalyst. The synthetic pathway involves the synthesis of pyrazoles with various electron donating and electron withdrawing functional groups containing hydrazines and 1,3‐diketones (70‐95% yields); then one step formation of 4‐iodo‐pyrazoles (59% yield) followed by modification via palladium catalyzed Suzuki‐Miyaura cross coupling reaction to obtain the desired biaryls substituted pyrazoles under mild reaction conditions with high efficiency and product purity (53‐70% yields). The biological activity was evaluated through in vitro analysis towards the antimicrobial activities against the growth of Staphylococcus Aureus (for Gram positive) and Pseudomonas Aeruginosa (for Gram negative) with minimum inhibitory concentration (MIC) values ranging from 225 to 850 μg/ml. Molecular docking studies of the compounds into the active site of thymidylate kinase receptor of Pseudomonas Aeruginosa PAO1 revealed notable information on the probable binding interaction.

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Section: ‐ Optimization Of Catalytic System For Pyrazole Synthesis[a]mentioning

confidence: 99%

An Unexplored Lewis Acidic Catalytic System for Synthesis of Pyrazole and its Biaryls Derivatives with Antimicrobial Activities through Cycloaddition‐Iodination‐Suzuki Reaction

et al. 2019

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“…Since those reports, organometallic Mannich reactions of this type have been intensively studied. The number of catalysts useable has grown considerably, and the scope has been extended by using SnCl 2 , Bi(OTf) 3 , La(OTf) 3 , Montmorillonite KSF clay, Selectfluor, LiClO 4 , [Bmim]BF 4 , Sc(OTf) 3 , polystyrene‐supported Yb salts, a polystyrene‐supported sulfonamide of glycine, maleic acid, BrS + Me 2 ,Br – , 2,4,6‐trichloro‐1,3,5‐triazine (TCT), sulfamic acid, camphorsulfonic acid (CSA), ZrOCl 2 , HClO 4 /SiO 2 , phosphomolybdic acid (PMA)/SiO 2 , CuI, HfCl 4 (prenyl), FeCl 3 , PMA, Bi(NO 3 ) 3 , and In(OTf) 3 …”

Section: Sp3 Nucleophilesmentioning

confidence: 99%

Multicomponent Mannich‐Like Reactions of Organometallic Species

2017

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A century after the pioneering works of Carl Mannich in 1917, the aminoalkylation of carbonylated compounds has become a classical reaction of organic chemistry. Thanks to its modular character, the so-called multicomponent Mannich reaction has found numerous applications throughout the fields of chemistry, especially for synthetic and biomedical purpose. After 100 years of good service, recent developments involving

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“…In general, Homoallylic amines are prepared either by the addition of organometallic reagents to imines or by nucleophillic addition of allylsilanes, allyltin, allylboron, or allyl germane reagents to imines (Keck and Enholm, 1985) in the presence of catalysts such as LiClO 4 , [(Yadav et al, 2002), Sn(OTf) 3 (Manoj Pandey et al, 2005), Bi(OTf) 3 ÁnH 2 O (Ollevier et al, 2003), PdCl 2 (PPh3) 2 (Nakamura et al, 1996). Recently, HClO 4 -SiO 2 (Nagarapu et al, 2007) have been employed for this transformation.…”

Section: Introductionmentioning

confidence: 99%

A novel series of homoallylic amines as potential antimicrobials

et al. 2011

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An efficient catalytic three-component reaction of aldehydes, amines, and allyltributylstannate has been successfully developed to produce homoallylic amines at 25°C, in excellent yields, in the presence of 1 mol% of trifluoroacetic acid an inexpensive and environmentally friendly catalyst. Newly synthesized compounds were confirmed by spectral studies. Compound 3o was characterized by single crystal X-ray analysis. All the compounds were also screened for their antimicrobial activity. Halogen-substituted compounds namely 3d, 3g, 3n, and 3o have showed excellent antibacterial activity.

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LiClO4-catalyzed three-component-coupling reactions: a facile synthesis of homoallylic amines

Cited by 32 publications

References 17 publications

An Unexplored Lewis Acidic Catalytic System for Synthesis of Pyrazole and its Biaryls Derivatives with Antimicrobial Activities through Cycloaddition‐Iodination‐Suzuki Reaction

An Unexplored Lewis Acidic Catalytic System for Synthesis of Pyrazole and its Biaryls Derivatives with Antimicrobial Activities through Cycloaddition‐Iodination‐Suzuki Reaction

Multicomponent Mannich‐Like Reactions of Organometallic Species

A novel series of homoallylic amines as potential antimicrobials

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