Organoiodine(iii) mediated intramolecular oxidative cyclization of 1-(3-arylisoquinolin-1-yl)-2-(arylmethylene)hydrazines to 5-aryl-3-(aryl)-[1,2,4]triazolo[3,4-a] isoquinolines

RSC Advances ◽  
2015 ◽  
Vol 5 (5) ◽  
pp. 3781-3785 ◽  
Author(s):  
Pitchai Manivel ◽  
Kamalakannan Prabakaran ◽  
Upasana Banerjee ◽  
Fazlur-Rahman Nawaz Khan ◽  
Euh Duck Jeong ◽  
...  
Keyword(s):  
Ambient Temperature ◽  
Bond Formation ◽  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Intramolecular Oxidative Cyclization

Intramolecular C–N bond formation is achieved through oxidative cyclization of 1-(3-arylisoquinolin-1-yl)-2-(arylmethylene)hydrazines, 3, in the presence of hypervalent iodine oxidant and dichloromethane at ambient temperature.

Convenient Synthesis of Oxazolo[5,4-h]pyrrolo[4,3,2-de]quino­lones via Hypervalent Iodine Mediated Intramolecular Oxidative Cyclization

Synthesis ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 4517-4522
Author(s):  
Li-Ping Sun ◽  
Chun-Meng Wang ◽  
Sheng-Wei Yang ◽  
Kai-Xiang Tang ◽  
Tian-Hong Gao ◽  
...  
Keyword(s):  
Functional Groups ◽  
Practical Method ◽  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Air Atmosphere ◽  
Convenient Synthesis ◽  
Reaction Proceeds ◽  
Intramolecular Oxidative Cyclization

A convenient and practical method has been developed for the synthesis of substituted oxazolo[5,4-h]pyrrolo[4,3,2-de]quinolones via the intramolecular oxidative cyclization by using PIFA as oxidant and TMSOTf as additive in DCE under an air atmosphere. The reaction proceeds in good yields and has good functional groups tolerance.

PhI(OAc)2-Mediated Regioselective Synthesis of 5-Guanidino-1,2,4-thiadiazoles and 1,2,4-Triazolo[1,5-a]pyridines via Oxidative N–S and N–N Bond Formation

Synthesis ◽  
2019 ◽  
Vol 51 (19) ◽  
pp. 3600-3610 ◽  
Author(s):  
Tumula Nagaraju ◽  
Palakodety Radha Krishna ◽  
Balasubramanian Sridhar ◽  
Nakka Mangarao
Keyword(s):  
Ambient Temperature ◽  
High Efficiency ◽  
Bond Formation ◽  
Oxidative Cyclization ◽  
Regioselective Synthesis ◽  
Pyridine Derivatives

An effective and expeditious approach for the construction of biologically important 5-guanidino-1,2,4-thiadiazole and 1,2,4-triazolo[1,5-a]pyridine derivatives has been developed. This new protocol involves the phenyliodine(III) diacetate [PhI(OAc)2]-mediated oxidative cyclization of thioureas/2-aminopyridines and imidates via N–S and N–N bond formation at ambient temperature. This method furnishes the versatile 5-guanidino-1,2,4-thiadiazoles and 1,2,4-triazolo[1,5-a]pyridines in a scalable manner with high efficiency and excellent regioselectivity.

Formation of Carbon-Oxygen Bond Mediated by Hypervalent Iodine Reagents Under Metal-free Conditions

2020 ◽  
Vol 17 ◽  
Author(s):  
Ayesha Jalil ◽  
Yaxin O Yang ◽  
Zhendong Chen ◽  
Rongxuan Jia ◽  
Tianhao Bi ◽  
...  
Keyword(s):  
Natural Products ◽  
Bond Formation ◽  
Building Blocks ◽  
Review Article ◽  
Hypervalent Iodine ◽  
Metal Free ◽  
Bioactive Natural Products ◽  
The Past ◽  
Oxygen Bond ◽  
Privileged Scaffolds

: Hypervalent iodine reagents are a class of non-metallic oxidants have been widely used in the construction of several sorts of bond formations. This surging interest in hypervalent iodine reagents is essentially due to their very useful oxidizing properties, combined with their benign environmental character and commercial availability from the past few decades ago. Furthermore, these hypervalent iodine reagents have been used in the construction of many significant building blocks and privileged scaffolds of bioactive natural products. The purpose of writing this review article is to explore all the transformations in which carbon-oxygen bond formation occurred by using hypervalent iodine reagents under metal-free conditions

Reaction Mechanism of a Nonheme Iron Enzyme Catalyzed Oxidative Cyclization via C–C Bond Formation

2018 ◽  
Vol 21 (1) ◽  
pp. 228-232 ◽  
Author(s):  
Wei-chen Chang ◽  
Zhi-Jie Yang ◽  
Yueh-Hua Tu ◽  
Tun-Cheng Chien
Keyword(s):  
Reaction Mechanism ◽  
Bond Formation ◽  
Oxidative Cyclization ◽  
Nonheme Iron

Double C–H Activation for the C–C bond Formation Reactions

2018 ◽  
Vol 15 (7) ◽  
pp. 882-903 ◽  
Author(s):  
Jialin Liu ◽  
Xiaoyu Xiong ◽  
Jie Chen ◽  
Yuntao Wang ◽  
Ranran Zhu ◽  
...  
Keyword(s):  
Molecular Design ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Hypervalent Iodine ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Direct Functionalization ◽  
Catalyzed Reactions ◽  
Medium Ring ◽  
Bond Formation Reactions

Background: Among the numerous bond-forming patterns, C–C bond formation is one of the most useful tools for building molecules for the chemical industry as well as life sciences. Recently, one of the most challenging topics is the study of the direct coupling reactions via multiple C–H bond cleavage/activation processes. A number of excellent reviews on modern C–H direct functionalization have been reported by Bergman, Bercaw, Yu and others in recent years. Among the large number of available methodologies, Pdcatalyzed reactions and hypervalent iodine reagent mediated reactions represent the most popular metal and non-metal involved transformations. However, the comprehensive summary of the comparison of metal and non-metal mediated transformations is still not available. Objective: The review focuses on comparing these two types of reactions (Pd-catalyzed reactions and hypervalent iodine reagent mediated reactions) based on the ways of forming new C–C bonds, as well as the scope and limitations on the demonstration of their synthetic applications. Conclusion: Comparing the Pd-catalyzed strategies and hypervalent iodine reagent mediated methodologies for the direct C–C bond formation from activation of C-H bonds, we clearly noticed that both strategies are powerful tools for directly obtaining the corresponding pruducts. On one hand, the hypervalent iodine reagents mediated reactions are normally under mild conditions and give the molecular diversity without the presence of transition-metal, while the Pd-catalyzed approaches have a broader scope for the wide synthetic applications. On the other hand, unlike Pd-catalyzed C-C bond formation reactions, the study towards hypervalent iodine reagent mediated methodology mainly focused on the stoichiometric amount of hypervalent iodine reagent, while few catalytic reactions have been reported. Meanwhile, hypervalent iodine strategy has been proved to be more efficient in intramolecular medium-ring construction, while there are less successful examples on C(sp3)–C(sp3) bond formation. In summary, we have demonstrated a number of selected approaches for the formation of a new C–C bond under the utilization of Pd-catalyzed reaction conditions or hyperiodine reagents. The direct activations of sp2 or sp3 hybridized C–H bonds are believed to be important strategies for the future molecular design as well as useful chemical entity synthesis.

Copper-Catalyzed C(sp3)–C(sp3) Bond Formation Using a Hypervalent Iodine Reagent: An Efficient Allylic Trifluoromethylation

2011 ◽  
Vol 133 (41) ◽  
pp. 16410-16413 ◽  
Author(s):  
Xi Wang ◽  
Yuxuan Ye ◽  
Songnan Zhang ◽  
Jiajie Feng ◽  
Yan Xu ◽  
...  
Keyword(s):  
Bond Formation ◽  
Hypervalent Iodine

Room Temperature, Metal-Free, Regio-Selective Arylselenation of Anilines Using Diselenides as Selenium Source

Synthesis ◽  
2022 ◽  
Author(s):  
Rekha Bai ◽  
Kamlesh Kumar Dabaria ◽  
Satpal Singh Badsara
Keyword(s):  
Ambient Temperature ◽  
Room Temperature ◽  
Bond Formation ◽  
Metal Free ◽  
Aniline Derivatives

A metal-free direct C-H selenation of aniline derivatives via an iodine catalysed C-Se bond formation using diselenides as a selenium source at ambient temperature is described. A variety of aniline derivatives underwent regio-selective C-H selenation with different diselenides to afford the corresponding aryl selenoethers in good to excellent yields.

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