Catalyst-Free Synthesis of Fused Triazolo-Diazepino[5,6-b]Quinoline Derivatives via a Sequential Ugi-4CR–Nucleophilic Substitution–Intramolecular Click Reaction

Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1095-1101 ◽  
Author(s):  
Saeed Balalaie ◽  
Aref Vaezghaemi ◽  
Nahid Zarezadeh ◽  
Frank Rominger ◽  
Hamid Bijanzadeh
Keyword(s):  
Nucleophilic Substitution ◽  
Click Reaction ◽  
Quinoline Derivatives ◽  
Wide Scope ◽  
Bond Forming ◽  
Catalyst Free ◽  
Forming Efficiency ◽  
High Bond

A convenient, post-transformational reaction has been ­developed for the construction of highly diversified quinoline-fused triazolo-diazepinones featuring four diversification points by employing a catalyst-free Ugi four-component–nucleophilic substitution–intra­molecular click cycloaddition sequence. This approach provides a wide scope of products with good yields and high bond-forming efficiency.

Synthesis of 3-Oxoisoindoline-1-carboxamides through Sequential Four-Component Ugi Reaction/Oxidative Nucleophilic Substitution of Hydrogen

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 861-865
Author(s):  
Saeed Balalaie ◽  
Ahmed Al-Harrasi ◽  
Kamran Amiri ◽  
Muhammad U. Anwar
Keyword(s):  
Nucleophilic Substitution ◽  
Aerobic Oxidation ◽  
Ugi Reaction ◽  
Nucleophilic Substitution Of Hydrogen ◽  
Reaction Conditions ◽  
Bond Forming ◽  
Reaction Proceeds ◽  
Forming Efficiency ◽  
High Bond ◽  
Directing Group

This paper describes a diversity-oriented approach to the formation of 3-oxoisoindoline-1-carboxamide derivatives utilizing the potential of the nitro group as a directing group. The reaction proceeds through a novel class of post-transformation reactions through a sequential four-component Ugi reaction/oxidative nucleophilic substitution of hydrogen. The 3-oxoisoindoline-1-carboxamide derivatives were synthesized in the presence of a base under mild reaction conditions with high regio- and chemoselectivity. The aerobic oxidation, high bond-forming efficiency, high atom economy, and good to excellent yields are the main advantages of this approach.

A one-pot synthesis of [1,2,3]triazolo[1,5-a]quinoxalines from 1-azido-2-isocyanoarenes with high bond-forming efficiency

2017 ◽  
Vol 53 (7) ◽  
pp. 1305-1308 ◽  
Author(s):  
Dengke Li ◽  
Tingting Mao ◽  
Jinbo Huang ◽  
Qiang Zhu
Keyword(s):  
One Pot ◽  
Efficient Approach ◽  
Bond Forming ◽  
One Pot Synthesis ◽  
Forming Efficiency ◽  
High Bond ◽  
Terminal Acetylenes

An efficient approach to prepare 1,2,3-triazolo[1,5-a]quinoxaline scaffolds, starting from 1-azido-2-isocyanoarenes and terminal acetylenes or substituted acetaldehydes, has been developed.

A Domino Approach for the Synthesis of 4-Carboxamide Oxazolines from Azirines

Synthesis ◽  
2021 ◽  
Author(s):  
Ali Nikbakht ◽  
Fariba Mohammadi ◽  
Mohammad Sadeq Mousavi ◽  
Kamran Amiri ◽  
Saeed Balalaie ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Ring Expansion ◽  
Target Product ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Bond Forming ◽  
Forming Efficiency ◽  
High Bond ◽  
Ring Expansion Reaction ◽  
Indium Catalyst

A regio- and the diastereoselective ring-expansion reaction of N-acyl aziridine has been described for the synthesis of 4-carboxamide oxazolines using InCl3. A domino Ugi-Joullié/ring expansion reaction of arylphenylazirines, isocyanides, and carboxylic acids led to the target product through N-acylaziridine intermediate in the presence of indium catalyst. The oxazolines were synthesized in moderate to excellent yields with high atom-economy and high bond-forming efficiency under mild reaction conditions.

scholarly journals Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

2016 ◽  
Vol 12 ◽  
pp. 2898-2905 ◽  
Author(s):  
Michal Medvecký ◽  
Igor Linder ◽  
Luise Schefzig ◽  
Hans-Ulrich Reissig ◽  
Reinhold Zimmer
Keyword(s):  
Click Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
High Efficacy ◽  
Carbon Bond ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed ◽  
Oxazine Derivatives

Iodination of carbohydrate-derived 3,6-dihydro-2H-1,2-oxazines of type 3 using iodine and pyridine in DMF furnished 5-iodo-substituted 1,2-oxazine derivatives 4 with high efficacy. The alkenyl iodide moiety of 1,2-oxazine derivatives syn-4 and anti-4 was subsequently exploited for the introduction of new functionalities at the C-5 position by applying palladium-catalyzed carbon–carbon bond-forming reactions such as Sonogashira, Heck, or Suzuki coupling reactions as well as a cyanation reaction. These cross-coupling reactions led to a series of 5-alkynyl-, 5-alkenyl-, 5-aryl- and 5-cyano-substituted 1,2-oxazine derivatives being of considerable interest for further synthetic elaborations. This was exemplarily demonstrated by the hydrogenation of syn-21 and anti-24 and by a click reaction of a 5-alkynyl-substituted precursor.

scholarly journals The Synthesis of the Locating Substitution Derivatives of Chitosan by Click Reaction at the 6-Position of Chitin

2015 ◽  
Vol 2015 ◽  
pp. 1-9 ◽  
Author(s):  
Yu Chen ◽  
Yanchun Ye ◽  
Yanyan Jing ◽  
YuanYuan Gao ◽  
Yanwen Guo ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
High Efficiency ◽  
Click Reaction ◽  
Macrocyclic Compound ◽  
Optimum Conditions ◽  
Structures And Properties ◽  
Acetyl Group ◽  
Novel Method ◽  
Derivatives Of

A novel method to prepare the macrocyclic compound locating substitution derivatives of chitosan was investigated, by using cyclodextrin as the model of macrocyclic compound. The method combines the advantages of activated 6-OH of chitin and high efficiency of click reaction. Chitin C6-OHp-toluenesulfonate (CTN-6-OTs) was generated and subsequently transferred to chitin C6-N3via nucleophilic substitution. Afterwards,β-cyclodextrin was immobilized at 6-OH of chitin via click reaction to afford CTN-6-CD. Ultimately, CTS-6-CD was obtained by removing the acetyl group of chitin unit. The structures and properties of these products were characterized by FTIR, TG, and XRD, respectively. It was found that CTN-6-CD synthesized at the optimum conditions has an immobilized loading of1.6126×10-4 mol/g and that of the corresponding CTS-6-CD, generated by removal of the acetyl group, was1.6891×10-4 mol/g.

AIE-active self-assemblies from a catalyst-free thiol-yne click reaction and their utilization for biological imaging

2018 ◽  
Vol 92 ◽  
pp. 61-68 ◽  
Author(s):  
Ruming Jiang ◽  
Meng Cao ◽  
Meiying Liu ◽  
Liangji Liu ◽  
Qiang Huang ◽  
...  
Keyword(s):  
Click Reaction ◽  
Biological Imaging ◽  
Catalyst Free ◽  
Free Thiol

Simple Chemical Modification Using Perfluoroalkyl‐Substituted Stable Nitrile N ‐Oxide on Bulk Surface via Catalyst‐Free Click Reaction

2020 ◽  
Vol 5 (17) ◽  
pp. 5312-5315 ◽  
Author(s):  
Chen‐Gang Wang ◽  
Sumitra Cheawchan ◽  
Airong Qiagedeer ◽  
Shunsuke Monjiyama ◽  
Satoshi Uchida ◽  
...  
Keyword(s):  
Chemical Modification ◽  
Click Reaction ◽  
Catalyst Free ◽  
Bulk Surface ◽  
Simple Chemical

A New Catalyst-Free Synthesis of 2,3-Dicarboxylic Ester Quinoline Derivatives

2018 ◽  
Vol 38 (2) ◽  
pp. 504 ◽  
Author(s):  
Bin Wang ◽  
Wenbo Ye ◽  
Zicong Yan ◽  
Changfeng Wan ◽  
Haoqing Hou ◽  
...  
Keyword(s):  
Quinoline Derivatives ◽  
Catalyst Free ◽  
Dicarboxylic Ester

Catalyst-Free Tandem Ring-Opening/Click Reaction of Acetylene-Bearing Donor–Acceptor Cyclopropanes

Synlett ◽  
2014 ◽  
Vol 25 (16) ◽  
pp. 2297-2300 ◽  
Author(s):  
Michael Kerr ◽  
Michelle Flisar ◽  
Michael Emmett
Keyword(s):  
Ring Opening ◽  
Click Reaction ◽  
Catalyst Free ◽  
Donor Acceptor
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