Convenient Synthesis of Benzofuro[3,2-b]quinolines from 1-Azadienes and Arynes

Synthesis ◽  
2021 ◽  
Author(s):  
Qi Wang ◽  
Yan Wang ◽  
Shi-Kai Tian
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Fluoride Ion ◽  
Metal Free ◽  
Convenient Synthesis

An efficient method has been developed for the synthesis of benzofuro[3,2-b]quinolines through tandem [4+2] cycloaddition/aromatization under transition-metal-free conditions. A range of aurone-derived N-tosyl-1-azadienes smoothly reacted with arynes, generated in situ via fluoride ion-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates, delivering structurally diverse benzofuro[3,2-b]quinolines in moderate to good yields.

Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2, 4-dicarboxylates from methylene isocyanides and propiolaldehyde

2021 ◽  
Author(s):  
Xiaoli Huo ◽  
Xiaojuan Chen ◽  
Liya Yu ◽  
Chong Zhang ◽  
Linghui Zeng ◽  
...  
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Transformation Process ◽  
Facile Synthesis ◽  
Direct Transformation ◽  
Metal Free

A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2, 4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and...

Insertion Reaction of 2-Halo-N-allylanilines with K2S Involving Trisulfur Radical Anion: Synthesis of Benzothiazole Derivatives under Transition-Metal-Free Conditions

Synthesis ◽  
2020 ◽  
Author(s):  
Yan-Wei Zhao ◽  
Shun-Yi Wang ◽  
Xin-Yu Liu ◽  
Tian Jiang ◽  
Weidong Rao
Keyword(s):  
Transition Metal ◽  
Radical Anion ◽  
Radical Cyclization ◽  
Transition Metal Catalysis ◽  
Insertion Reaction ◽  
Metal Catalysis ◽  
Metal Free ◽  
Benzothiazole Derivatives

AbstractA synthesis of benzothiazole derivatives through the reaction of 2-halo-N-allylanilines with K2S in DMF is developed. The trisulfur radical anion S3·–, which is generated in situ from K2S in DMF, initiates the reaction without transition-metal catalysis or other additives. In addition, two C–S bonds are formed and heteroaromatization of benzothiazole is triggered by radical cyclization and H-shift.

Diiiodine/Potassium Persulfate Mediated Synthesis of 1,2,3-Thiadiazoles from N-Tosylhydrazones and a Thiocyanate Salt as a Sulfur Source under Transition-Metal-Free Conditions

Synlett ◽  
2021 ◽  
Author(s):  
Yadong Sun ◽  
Ablimit Abdukader ◽  
Yuhan Lu ◽  
Chenjiang Liu
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Room Temperature ◽  
Functional Group ◽  
Ammonium Thiocyanate ◽  
Potassium Persulfate ◽  
Sulfur Source ◽  
Coupling Reactions ◽  
Wide Scope ◽  
Metal Free

AbstractA highly efficient method for the synthesis of 1,2,3-thiadiazoles has been developed by utilizing readily available tosylhydrazones and ammonium thiocyanate with ecofriendly EtOH as the solvent at room temperature. The reaction shows a wide scope of substrates and good functional-group tolerance. This protocol can be scaled up to a gram level and can be applied to coupling reactions with 4-(4-bromophenyl)-1,2,3-thiadiazole as the substrate.

Recent Developments in Transition-Metal-Free Functionalization and Derivatization Reactions of Pyridines

Synlett ◽  
2020 ◽  
Author(s):  
Lei Jiao ◽  
Fei-Yu Zhou
Keyword(s):  
Transition Metal ◽  
Structural Motif ◽  
Metal Exchange ◽  
Coupling Reactions ◽  
Phosphonium Salts ◽  
Metal Free ◽  
Radical Coupling ◽  
In Situ Activation ◽  
Recent Developments

AbstractPyridine is an important structural motif that is prevalent in natural products, drugs, and materials. Methods that functionalize and derivatize pyridines have gained significant attention. Recently, a large number of transition-metal-free reactions have been developed. In this review, we provide a brief summary of recent advances in transition-metal-free functionalization and derivatization reactions of pyridines, categorized according to their reaction modes.1 Introduction2 Metalated Pyridines as Nucleophiles2.1 Deprotonation2.2 Halogen–Metal exchange3 Activated Pyridines as Electrophiles3.1 Asymmetric 2-Allylation by Chiral Phosphite Catalysis3.2 Activation of Pyridines by a Bifunctional Activating Group3.3 Alkylation of Pyridines by 1,2-Migration3.4 Alkylation of Pyridines by [3+2] Addition3.5 Pyridine Derivatization by Catalytic In Situ Activation Strategies3.6 Reactions via Heterocyclic Phosphonium Salts4 Radical Reactions for Pyridine Functionalization4.1 Pyridine Functionalization through Radical Addition Reactions4.2 Pyridine Functionalization through Radical–Radical Coupling Reactions5 Derivatization of Pyridines through the Formation of Meisenheimer-Type Pyridyl Anions6 Conclusion

Hydride-Induced Anionic Cyclization: An Efficient Method for the Synthesis of 6-H-Phenanthridines via a Transition-Metal-Free Process

2015 ◽  
Vol 17 (6) ◽  
pp. 1613-1616 ◽  
Author(s):  
Wei-Lin Chen ◽  
Chun-Yuan Chen ◽  
Yan-Fu Chen ◽  
Jen-Chieh Hsieh
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Metal Free ◽  
Free Process

ChemInform Abstract: In situ Generation of PhI+CF3and Transition-Metal-Free Oxidative sp2C-H Trifluoromethylation.

ChemInform ◽  
2013 ◽  
Vol 44 (48) ◽  
pp. no-no
Author(s):  
Cong Xu ◽  
Jingxin Liu ◽  
Wenbo Ming ◽  
Yingjie Liu ◽  
Jun Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
In Situ Generation

ChemInform Abstract: Transition-Metal-Free Arylation of N-Alkyl-tetrahydroisoquinolines under Oxidative Conditions: A Convenient Synthesis of C1-Arylated Tetrahydroisoquinoline Alkaloids.

ChemInform ◽  
2015 ◽  
Vol 46 (13) ◽  
pp. no-no
Author(s):  
Kamal Nain Singh ◽  
Satinder V. Kessar ◽  
Paramjit Singh ◽  
Pushpinder Singh ◽  
Manjot Kaur ◽  
...  
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
Convenient Synthesis
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