Copper-catalyzed coupling of anthranils and α-keto acids: direct synthesis of α-ketoamides

2019 ◽  
Vol 17 (24) ◽  
pp. 5902-5907 ◽  
Author(s):  
Ping-Gui Li ◽  
Hao Zhu ◽  
Min Fan ◽  
Cheng Yan ◽  
Kai Shi ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Bond Formation ◽  
Aldehyde Group ◽  
Keto Acids

Copper-catalyzed coupling of α-keto acids with anthranils is reported for the synthesis of α-ketoamides bearing an aldehyde group via N–O/C–O bond cleavages and C–N bond formation.

scholarly journals N–N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights

2018 ◽  
Vol 20 (16) ◽  
pp. 4736-4739 ◽  
Author(s):  
Jie S. Zhu ◽  
Niklas Kraemer ◽  
Marina E. Shatskikh ◽  
Clarabella J. Li ◽  
Jung-Ho Son ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Bond Formation ◽  
Primary Amines

scholarly journals PIDA-mediated intramolecular oxidative C–N bond formation for the direct synthesis of quinoxalines from enaminones

RSC Advances ◽  
2019 ◽  
Vol 9 (14) ◽  
pp. 7718-7722 ◽  
Author(s):  
Hong Zhang ◽  
Jinhai Shen ◽  
Zhenhui Yang ◽  
Xiuling Cui
Keyword(s):  
Direct Synthesis ◽  
Bond Formation ◽  
Hypervalent Iodine ◽  
Mild Conditions

An expedient hypervalent iodine(iii)-mediated approach to obtain substituted quinoxalines from readily available enaminones has been developed under mild conditions.

scholarly journals Efficient Copper Catalyzed Multi-component Synthesis of N-acyl amidines via Acyl Nitrenes

2019 ◽  
Author(s):  
K.M. van Vliet ◽  
Lara H. Polak ◽  
Maxime A. Siegler ◽  
J.I. van der Vlugt ◽  
Célia Fonseca Guerra ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Bond Formation ◽  
Organometallic Complexes ◽  
Biologically Active ◽  
Mechanistic Studies ◽  
Copper Acetylide ◽  
Substrate Conversion ◽  
Cu Catalyst ◽  
New Type ◽  
Synthetic Routes

Direct synthetic routes to amidines are desired, as they are widely present in many biologically active compounds and organometallic complexes. N-Acyl amidines in particular can be used as a starting material for the synthesis of heterocycles and have several other applications. Here, we describe a fast and practical copper catalyzed 3-component reaction of aryl acetylenes, amines and easily accessible 1,4,2-dioxazol-5-ones to N-acyl amidines, generating CO<sub>2</sub> as the only by-product. Transformation of the dioxazolones on the Cu-catalyst generates acyl nitrenes that rapidly insert into the copper acetylide Cu-C bond rather than undergoing an undesired Curtius rearrangement. For non-aromatic dioxazolones, [Cu(OAc)(Xantphos)] is a superior catalyst for this transformation, leading to full substrate conversion within 10 minutes. For the direct synthesis of N-benzoyl amidine derivatives from aromatic dioxazolones, [Cu(OAc)(Xantphos)] proved to be inactive, but moderate to good yields were obtained when using simple CuI as the catalyst. Mechanistic studies revealed the aerobic instability of one of the intermediates at low catalyst loadings, but the reaction could still be performed in air for most substrates when using catalyst loadings of 5 mol%. The herein reported procedure does not only provide a new, practical and direct route to N-acyl amidines, but also represents a new type of<br>C-N bond formation.

Synthesis of 6-substituted indoloquinazolinones from arynes and 2-acyl-4-quinazolinones: a transition-metal free C–N and C–C bond formation strategy

2020 ◽  
Vol 44 (41) ◽  
pp. 17938-17953
Author(s):  
Abhilash Sharma ◽  
Pranjal Gogoi
Keyword(s):  
Transition Metal ◽  
Direct Synthesis ◽  
Bond Formation ◽  
Reaction Vessel ◽  
Metal Free ◽  
Synthetic Strategy ◽  
Single Reaction

A versatile transition-metal free synthetic strategy has been developed for the direct synthesis of 6-substituted indoloquinazolinones from 2-acyl-4-quinazolinones and aryne precursors. This cascade strategy proceeds via successive C–N and C–C bond formation in a single reaction vessel.

Copper nanoparticles supported on charcoal mediated one-pot three-component synthesis of N-substituted-2H-indazoles via consecutive condensation C–N and N–N bond formation

2019 ◽  
Vol 97 (4) ◽  
pp. 303-309 ◽  
Author(s):  
Reza Khalifeh ◽  
Faranak Karimzadeh
Keyword(s):  
Copper Nanoparticles ◽  
Sodium Azide ◽  
Direct Synthesis ◽  
Bond Formation ◽  
Primary Amines ◽  
Title Reaction ◽  
One Pot

An efficient and straightforward protocol for direct synthesis of 2H-indazoles is achieved from consecutive condensation of 2-halobenzaldehydes, primary amines, and sodium azide catalyzed by heterogeneous copper nanoparticles on charcoal (Cu/C) is achieved. The recoverable heterogeneous copper nanoparticles on charcoal (Cu/C) catalyst exhibited an impressive activity for the title reaction without any additives (expensive ligands, etc.). A series of structurally diverse 2H-indazoles were prepared in good to excellent yields from easily accessible starting materials by employing this protocol.

Ligand- and catalyst-free intramolecular C-S bond formation: direct access to indalothiochromen- 4-ones

2015 ◽  
Vol 21 (3) ◽  
pp. 159-163 ◽  
Author(s):  
T.A. Jenifer Vijay ◽  
Nagarakere C. Sandhya ◽  
C.S. Pavankumar ◽  
Kanchugarakoppal S. Rangappa ◽  
Kempegowda Mantelingu
Keyword(s):  
Functional Group ◽  
Direct Synthesis ◽  
Bond Formation ◽  
Direct Access ◽  
Mild Conditions ◽  
Catalyst Free

AbstractAn efficient ligand- and catalyst-free intramolecular S-arylation leading to the direct synthesis of indalothiochromen-4-ones from simple dithioesters under mild conditions has been developed. This method is particularly noteworthy given its experimental simplicity, high generality, and good functional group toleration.

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