Unprecedented synthesis of 1,2,3-triazolo-cinnolinone via Sonogashira coupling and intramolecular cyclization

2018 ◽  
Vol 16 (26) ◽  
pp. 4840-4848 ◽  
Author(s):  
Avnish Kumar ◽  
Dharmendra Kumar Tiwari ◽  
Balasubramanian Sridhar ◽  
Pravin R. Likhar
Keyword(s):  
Intramolecular Cyclization ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
One Pot

An unprecedented copper mediated one-pot sequential synthesis of 1,2,3-triazolo cinnolinone derivatives from 2-halo-phenyl triazoles and terminal alkynes has been reported.

One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling–intramolecular cyclization

2019 ◽  
Vol 9 (22) ◽  
pp. 6471-6481 ◽  
Author(s):  
Narasimha Swamy Thirukovela ◽  
Ramesh Balaboina ◽  
Vinayak Botla ◽  
Ravinder Vadde ◽  
Sreekantha Babu Jonnalagadda ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Pd Nanoparticles ◽  
Environmentally Benign ◽  
Water Medium ◽  
Sonogashira Coupling ◽  
One Pot ◽  
Peg 400 ◽  
Sequential Coupling ◽  
Substituted Pyrazoles

Catalyst efficacy of in situ generated Pd-nanoparticles in the regioselective one-pot synthesis of substituted pyrazoles and isoxazoles via sequential coupling-cyclization methodology in environmentally benign medium is described.

scholarly journals One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation

2021 ◽  
Vol 8 ◽  
Author(s):  
Fa-Jie Chen ◽  
Zhenguo Hua ◽  
Jianhui Chen ◽  
Jiajia Chen ◽  
Daesung Lee ◽  
...  
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Copper Catalyst ◽  
High Yield ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Acid Chlorides ◽  
Triflic Acid ◽  
One Pot

Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.

Brønsted acid-catalyzed synthesis of carbazoles from 2-substituted indoles

2014 ◽  
Vol 1 (10) ◽  
pp. 1197-1200 ◽  
Author(s):  
Qingjiang Li ◽  
Xiao-Shui Peng ◽  
Henry N. C. Wong
Keyword(s):  
Intramolecular Cyclization ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Efficient Approach ◽  
Brönsted Acid ◽  
Acid Catalyzed

A simple and efficient approach for the synthesis of disubstituted carbazoles has been developed from o-haloanilines and terminal alkynes using a two-step strategy, namely, Sonogashira coupling and intramolecular cyclization.

A One-Pot Method for the Synthesis of Phenylalkynyl-Substituted Terminal Alkynes by Deprotection/Stannylation followed by a Migita–Kosugi–Stille coupling

2018 ◽  
Vol 42 (5) ◽  
pp. 235-238 ◽  
Author(s):  
Li-fen Peng ◽  
Bing-hao Wang ◽  
Ming Wang ◽  
Zi-long Tang ◽  
Yan-zi Jiang ◽  
...  
Keyword(s):  
Phosphine Oxide ◽  
Functional Group ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Synthetic Route ◽  
Stille Coupling ◽  
Reaction Conditions ◽  
One Pot

A practical one-pot approach for the synthesis of arylalkynyl-substituted terminal alkynes has been developed through a deprotection/ stannylation of a phenylethynyl phosphine oxide followed by Migita–Kosugi–Stille coupling, avoiding the longer synthetic route involving repeated deprotection/Sonogashira coupling. Other features of this approach include mild reaction conditions, excellent yields, facile isolation of products and wide functional group tolerance.

scholarly journals Nickel-Catalyzed Deaminative Sonogashira Coupling of Alkylpyridinium Salts Enabled by a New NN2 Pincer Ligand

2020 ◽  
Author(s):  
Xingjie Zhang ◽  
Di Qi ◽  
Chenchen Jiao ◽  
Xiaopan Liu ◽  
Guisheng Zhang
Keyword(s):  
High Efficiency ◽  
Materials Science ◽  
Alkylating Agents ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Pincer Ligand ◽  
One Pot ◽  
Alkyl Amines ◽  
Sonogashira Reactions ◽  
First Time

Abstract Alkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Herein, a novel transformation is disclosed that enables the coupling of terminal alkynes with alkylpyridinium salts under Ni-catalysis. Key to the success of this coupling was the development of a new and readily accessible amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions for the first time, and leads to diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrates scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals.

One-Pot Synthesis of Naphtho[1′,2′:4,5]imidazo[1,2-a ]pyridin-5-yl(aryl)methanones through Sequential Sonogashira Coupling/Alkyne-Carbonyl Metathesis

2017 ◽  
Vol 2017 (27) ◽  
pp. 4026-4034 ◽  
Author(s):  
Mirza Feroz Baig ◽  
Siddiq Pasha Shaik ◽  
Namballa Hari Krishna ◽  
Neeraj Kumar Chouhan ◽  
Abdullah Alarifi ◽  
...  
Keyword(s):  
Sonogashira Coupling ◽  
One Pot ◽  
One Pot Synthesis

ChemInform Abstract: An Efficient, General Synthesis of 2-Substituted 3,6-Dihydropyrrolo[3,2-e]indoles Involving One-Pot Sonogashira Coupling and Cyclization.

ChemInform ◽  
2013 ◽  
Vol 44 (32) ◽  
pp. no-no
Author(s):  
Moumita Rakshit ◽  
Taraknath Kundu ◽  
Gandhi K. Kar ◽  
Manas Chakrabarty
Keyword(s):  
Sonogashira Coupling ◽  
One Pot ◽  
General Synthesis
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