Metal-Free Synthesis of 2-Substituted Quinolines via High Chemoselective Domino Condensation/Aza-Prins Cyclization/Retro-Aldol between 2-Alkenylanilines with β-Ketoesters

2020 ◽  
Vol 85 (21) ◽  
pp. 14042-14054
Author(s):  
Jiang Nan ◽  
Pu Chen ◽  
Yuxin Zhang ◽  
Yun Yin ◽  
Bo Wang ◽  
...  
Keyword(s):  
Prins Cyclization ◽  
Metal Free ◽  
Substituted Quinolines

ChemInform Abstract: Green Chemistry: Solvent- and Metal-Free Prins Cyclization. Application to Sequential Reactions.

ChemInform ◽  
2012 ◽  
Vol 43 (17) ◽  
pp. no-no
Author(s):  
Damien Clarisse ◽  
Beatrice Pelotier ◽  
Olivier Piva ◽  
Fabienne Fache
Keyword(s):  
Green Chemistry ◽  
Prins Cyclization ◽  
Metal Free ◽  
Sequential Reactions

Photochemistry of ortho-Azidocinnamoyl Derivatives: Facile and Modular Synthesis of 2-Acylated Indoles and 2-Substituted Quinolines under Solvent Control

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2614-2618 ◽  
Author(s):  
S. Chassaing ◽  
S. Chaabouni ◽  
N. Pinkerton ◽  
S. Abid ◽  
C. Galaup
Keyword(s):  
Heterocycle Synthesis ◽  
Metal Free ◽  
Modular Synthesis ◽  
Substituted Quinolines ◽  
Solvent Control

The light-promoted potential of ortho-azidocinnamoyl compounds is evaluated for heterocycle synthesis. Depending on the nature of the solvent, 2-acylated indoles were obtained under aprotic conditions, whereas the use of a protic medium led to 2-substituted quinolines. The synthetic significance of this metal-free method is that, by simply changing the solvent, the reaction outcome can be directed towards different key heterocyclic scaffolds.

Synthesis of Multibromo-Substituted Quinolines by NBS-Mediated Cascade Electrophilic Bromination/Cyclization of N-(3-Phenylprop-2-ynyl)anilines

Synthesis ◽  
2021 ◽  
Author(s):  
Ruchun Yang ◽  
Qiang Xiao ◽  
Si Deng ◽  
Wenliang Ouyang ◽  
Jiang Bai ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Sonogashira Coupling ◽  
Metal Free ◽  
Cascade Cyclization ◽  
Mild Conditions ◽  
Free Process ◽  
Substituted Quinolines ◽  
Sonogashira Coupling Reaction ◽  
Electrophilic Bromination

AbstractA new and convenient protocol is presented here for the synthesis of 3,6,8-tribromoquinolines via cascade cyclization of N-(3-phenylprop-2-ynyl)anilines employing N-bromosuccinimide as an electrophile. The metal-free process is carried out under mild conditions and is compatible with a variety of substituents. The Sonogashira coupling reaction regioselectively occurs at position C-6 of the obtained products.

Recent Advances in Transition Metal Free Synthetic Protocols for Quinoline Derivatives

2020 ◽  
Vol 24 (16) ◽  
pp. 1815-1852
Author(s):  
Rukhsana Tabassum ◽  
Muhammad Ashfaq ◽  
Hiroyuki Oku
Keyword(s):  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Pharmaceutical Chemistry ◽  
Quinoline Derivatives ◽  
Metal Free ◽  
Substituted Quinolines ◽  
Privileged Scaffold ◽  
Synthetic Routes ◽  
Therapeutic Activities ◽  
Insight Into

The quinoline moiety is a privileged scaffold among heterocyclic compounds that is an important construction motif in the fields of pharmaceutical chemistry. Quinoline molecule possesses a variety of therapeutic activities like antiviral, antimalarial, antibacterial, antitumor, anticancer, antioxidant antihypertensive, antifungal, anthelmintic, cardiotonic, anticonvulsant and anti-inflammatory. This review provides an insight into recent development in transition metal free novel and modified conventional synthetic routes to yield a wide variety of substituted quinolines.

Substrate selective synthesis of indole, tetrahydroquinoline and quinoline derivatives via intramolecular addition of hydrazones and imines

2018 ◽  
Vol 5 (7) ◽  
pp. 1170-1175 ◽  
Author(s):  
Rahul K. Maurya ◽  
Om P. S. Patel ◽  
Devireddy Anand ◽  
Prem P. Yadav
Keyword(s):  
Transition Metal ◽  
Selective Synthesis ◽  
Quinoline Derivatives ◽  
Metal Free ◽  
Substituted Quinolines

A transition-metal-free, substrate selective synthesis of 2,3-diaryl indoles, 4-hydrazono-tetrahydroquinolines and substituted quinolines has been developed.

ChemInform Abstract: Solvent-Free, Metal-Free, Aza-Prins Cyclization: Unprecedented Access to δ-Sultams.

ChemInform ◽  
2013 ◽  
Vol 44 (25) ◽  
pp. no-no
Author(s):  
Damien Clarisse ◽  
Beatrice Pelotier ◽  
Fabienne Fache
Keyword(s):  
Solvent Free ◽  
Prins Cyclization ◽  
Metal Free ◽  
Free Metal

ChemInform Abstract: Metal-Free Synthesis of Highly Substituted Quinolines under Mild Conditions.

ChemInform ◽  
2016 ◽  
Vol 47 (43) ◽  
Author(s):  
Rakesh Natarajan ◽  
Peruparambil A. Unnikrishnan ◽  
Sandhya Radhamani ◽  
John P. Rappai ◽  
Sreedharan Prathapan
Keyword(s):  
Metal Free ◽  
Mild Conditions ◽  
Substituted Quinolines

Green chemistry: solvent- and metal-free Prins cyclization. Application to sequential reactions

2012 ◽  
Vol 48 (1) ◽  
pp. 157-159 ◽  
Author(s):  
Damien Clarisse ◽  
Béatrice Pelotier ◽  
Olivier Piva ◽  
Fabienne Fache
Keyword(s):  
Green Chemistry ◽  
Prins Cyclization ◽  
Metal Free ◽  
Sequential Reactions

Boron-Catalyzed Hydrogenative Reduction of Substituted Quinolines to Tetrahydroquinolines with Hydrosilanes

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2396-2400 ◽  
Author(s):  
Sehoon Park ◽  
Sukbok Chang ◽  
Narasimhulu Gandhamsetty
Keyword(s):  
Initial Step ◽  
Reducing Agents ◽  
Catalytic Cycle ◽  
Transfer Hydrogenation ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Substituted Quinolines ◽  
Optimized Conditions ◽  
Hydroxy Groups

A metal-free procedure for the hydrogenative reduction of substituted N-heteroaromatics has been developed by using hydrosilanes as reducing agents. The optimized conditions were successfully applied to the reactions of quinolines, quinoxalines, and quinoline N-oxides. They were also effective for the reduction of quinolines bearing amino or hydroxy groups, where H2 was evolved through dehydrogenative silylation of the amine or hydroxy moieties. Preliminary mechanistic studies revealed that the initial step in the catalytic cycle involves 1,4-addition of the hydrosilane to the quinoline to give a 1,4-dihydroquinoline; this is followed by (transfer) hydrogenation to deliver the tetrahydroquinoline as the final product.

Metal-free synthesis of highly substituted quinolines under mild conditions

2016 ◽  
Vol 57 (27-28) ◽  
pp. 2981-2984 ◽  
Author(s):  
Rakesh Natarajan ◽  
Peruparambil A. Unnikrishnan ◽  
Sandhya Radhamani ◽  
John P. Rappai ◽  
Sreedharan Prathapan
Keyword(s):  
Metal Free ◽  
Mild Conditions ◽  
Substituted Quinolines
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