Decarboxylative dipropargylation of primary amines with propiolic acids and formaldehyde via metal-free coupling

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

The Journal of Organic Chemistry ◽

10.1021/acs.joc.7b01507 ◽

2017 ◽

Vol 82 (16) ◽

pp. 8617-8627 ◽

Cited By ~ 12

Author(s):

Meng Zhang ◽

Hui-Juan Wang ◽

Fa-Bao Li ◽

Xin-Xin Zhong ◽

Yong-Shun Huang ◽

...

Keyword(s):

Aromatic Aldehydes ◽

Primary Amines ◽

Metal Free

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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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Mild Access to N-Formylation of Primary Amines using Ethers as C1 Synthons under Metal-Free Conditions

Advanced Synthesis & Catalysis ◽

10.1002/adsc.201800783 ◽

2018 ◽

Vol 360 (20) ◽

pp. 3960-3968 ◽

Cited By ~ 11

Author(s):

Mohana Reddy Mutra ◽

Ganesh Kumar Dhandabani ◽

Jeh-Jeng Wang

Keyword(s):

Primary Amines ◽

Metal Free

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Metal-Free Oxidative C(sp3)–N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Synlett ◽

10.1055/s-0036-1591544 ◽

2018 ◽

Vol 29 (07) ◽

pp. 912-917 ◽

Cited By ~ 1

Author(s):

Parviz Ranjbar ◽

Narjes Rezaei ◽

Ehsan Sheikhi

Keyword(s):

Oxidative Cyclization ◽

Cyclization Reaction ◽

Primary Amines ◽

Isatoic Anhydride ◽

Reaction Conditions ◽

Coupling Process ◽

Benzylic Alcohols ◽

Metal Free ◽

Novel Synthesis

A metal-free oxidative C(sp3)–N coupling process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. The reaction between primary amines, isatoic anhydride, and benzylic alcohols in the presence of HBr in DMSO at 80 °C affords 2,3-dihydroquinazolin-4(1H)-ones in excellent yields. Under these reaction conditions, benzylic alcohols react with in situ generated bromodimethylsulfonium bromide to form alkoxysulfonium intermediates. These intermediates undergo an oxidative cyclization reaction with primary amines and isatoic anhydride to produce the title products.

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A simple route towards the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from primary amines and 1,3-dicarbonyl compounds under metal-free conditions

Organic & Biomolecular Chemistry ◽

10.1039/c9ob01156k ◽

2019 ◽

Vol 17 (25) ◽

pp. 6148-6152 ◽

Cited By ~ 3

Author(s):

Ningxin Guo ◽

Xiufen Liu ◽

Hongyan Xu ◽

Xi Zhou ◽

Huaiqing Zhao

Keyword(s):

Primary Amines ◽

Dicarbonyl Compounds ◽

Simple Route ◽

Metal Free ◽

One Step

A metal-free protocol for the synthesis of fully substituted 1,2,3-triazoles in a one-step reaction from easily available primary amines, 1,3-dicarbonyl compounds and tosyl azide was developed under air.

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