Synthesis of 2-Aryl-5-alkyl-fulleropyrrolidines: Metal-Free-Mediated Reaction of [60]Fullerene with Aromatic Aldehydes and Inactive Primary Amines

Herein we describe a very useful application of the readily available trifunctional aromatic ketone methyl-2-(2-bromoacetyl)benzoate in reactions with primary amines. An unexpected in situ air oxidation that follows a cascade process allowed the access to a series of isoquinoline-1,3,4(2H)-triones, a class of heterocyclic compounds of great interest containing an oxygen-rich heterocyclic scaffold. A modification of the original protocol, utilizing a Staudinger reaction in the presence of trimethylphosphine, was necessary for the synthesis of Caspase inhibitor trione with free NH group.

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A general metal-free route towards the synthesis of 1,2,3-triazoles from readily available primary amines and ketones

Chemical Communications ◽

10.1039/c5cc08347h ◽

2016 ◽

Vol 52 (14) ◽

pp. 2885-2888 ◽

Cited By ~ 49

Author(s):

Joice Thomas ◽

Sampad Jana ◽

Jubi John ◽

Sandra Liekens ◽

Wim Dehaen

Keyword(s):

Natural Products ◽

Primary Amines ◽

Metal Free ◽

Amino Esters

A metal-free route towards different 1,2,3-triazole heterocycles was accomplished by using inexpensive and readily available ketones and primary amines. This reaction is very general and was extended to functionalize different amino esters, dendrimers and natural products.

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ChemInform Abstract: Direct Amination of 2-(1-Tosylalkyl)phenols with Aqueous Ammonia: A Metal-Free Synthesis of Primary Amines.

ChemInform ◽

10.1002/chin.201526081 ◽

2015 ◽

Vol 46 (26) ◽

pp. no-no

Author(s):

Bo Wu ◽

Xiang Gao ◽

Mu-Wang Chen ◽

Yong-Gui Zhou

Keyword(s):

Aqueous Ammonia ◽

Primary Amines ◽

Direct Amination ◽

Metal Free

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ChemInform Abstract: A Metal-Free Oxidative Amination of Benzoxazoles with Primary Amines and Ammonia.

ChemInform ◽

10.1002/chin.201217130 ◽

2012 ◽

Vol 43 (17) ◽

pp. no-no

Author(s):

Ulrich Kloeckner ◽

Nicole M. Weckenmann ◽

Boris J. Nachtsheim

Keyword(s):

Primary Amines ◽

Oxidative Amination ◽

Metal Free

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Base-promoted aerobic oxidative synthesis of fused 1,3,5-triazines under metal-free conditions

Green Chemistry ◽

10.1039/d0gc02691c ◽

2020 ◽

Vol 22 (20) ◽

pp. 6778-6782

Author(s):

Jinjin Chen ◽

Zhaozhao Sun ◽

Fuhong Xiao ◽

Guo-Jun Deng

Keyword(s):

Aerobic Oxidation ◽

Aromatic Aldehydes ◽

Ammonium Iodide ◽

Metal Free

An efficient base-promoted aerobic oxidation procedure for the synthesis of fused 1,3,5-triazines from 2-aminobenzimidazoles, aromatic aldehydes, and ammonium iodide under metal-free conditions has been developed.

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ChemInform Abstract: A Formal Metal-Free N-Arylation via the Schmidt Reaction of Aromatic Aldehydes with an Azido Amine.

ChemInform ◽

10.1002/chin.201326036 ◽

2013 ◽

Vol 44 (26) ◽

pp. no-no

Author(s):

Peiming Gu ◽

Jian Sun ◽

Xiao-Yan Kang ◽

Ming Yi ◽

Xue-Qiang Li ◽

...

Keyword(s):

Aromatic Aldehydes ◽

Schmidt Reaction ◽

Metal Free

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Synthesis of Bis-2,3-dihydroquinazolin-4(1H)-ones and 2,3-Dihydroquinazolin-4(1H)-ones Derivatives with the Aid of Silica-Supported Preyssler Nanoparticles

Organic Chemistry International ◽

10.1155/2013/848237 ◽

2013 ◽

Vol 2013 ◽

pp. 1-14 ◽

Cited By ~ 4

Author(s):

Ali Gharib ◽

Bibi Robabeh Hashemipour Khorasani ◽

Manouchehr Jahangir ◽

Mina Roshani ◽

Reza Safaee

Keyword(s):

Primary Amine ◽

Ammonium Carbonate ◽

Aromatic Aldehydes ◽

Product Yield ◽

Primary Amines ◽

Isatoic Anhydride ◽

One Pot ◽

High Yields ◽

First Time

One-pot three-component condensation of isatoic anhydride with primary amines or ammonium carbonate and aromatic aldehydes in refluxing ethanol in the presence of catalytic amounts of silica-supported preyssler nanoparticles (SPNP) afforded the corresponding 2,3-dihydroquinazolin-4(1H)-ones in high yields, and bis-dihydroquinazolinones were synthesized for the first time by a novel pseudo-five-component condensation of isatoic anhydride, a primary amine, and a dialdehyde in water. The catalyst is reusable and can be applied several times without any decrease in product yield.

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