Dioxygen-triggered oxidative cleavage of the C–S bond towards C–N bond formation

2019 ◽  
Vol 55 (82) ◽  
pp. 12332-12335 ◽  
Author(s):  
Zongchao Lv ◽  
Huamin Wang ◽  
Zhicong Quan ◽  
Yuan Gao ◽  
Aiwen Lei
Keyword(s):  
Heterocyclic Compounds ◽  
Bond Formation ◽  
Oxidative Cleavage

Dioxygen-triggered oxidative cleavage of C–S bonds has been achieved, delivering a series of N-containing heterocyclic compounds that are frequently found in pesticides and pharmaceuticals.

Pd-catalysed general access to 7-membered N/O-heterocyclic compounds as potential agents against inflammation

2021 ◽  
Vol 57 (78) ◽  
pp. 10091-10094
Author(s):  
B. Thirupataiah ◽  
Gangireddy Sujeevan Reddy ◽  
Guntipally Mounika ◽  
Jetta Sandeep Kumar ◽  
Kazi Amirul Hossain ◽  
...  
Keyword(s):  
Heterocyclic Compounds ◽  
Bond Formation ◽  
Regioselective Synthesis

A Pd-catalysed regioselective synthesis of 4,5-disubstituted 7-membered N/O-heterocycles was achieved via the 7-endo-dig cyclization followed by C–C bond formation of 2-(1-alkynyl)phenylacetamide.

Recent Development in N-Auxilixary-Assisted Intramolecular Amination for Amine Substrates

Synlett ◽  
2015 ◽  
Vol 26 (08) ◽  
pp. 997-1002 ◽  
Author(s):  
Yingsheng Zhao ◽  
Chao Wang ◽  
Jian Han
Keyword(s):  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Bond Formation ◽  
Direct Coupling ◽  
Significant Progress ◽  
Palladium Catalyzed ◽  
Directing Group

Direct coupling of N–H with C–H has aroused great attention in the last decades; during which the directing-group-assisted intramolecular C–N bond formation via transition metal has been achieved significant progress. Herein, we highlight the recent development in the directing-group-assisted intramolecular amination for amine substrates to build the important N-containing heterocyclic compounds.1 Introduction2 Triflamide-Promoted Intramolecular Amination3 Picolinamide-Assisted Intramolecular Amination4 Palladium-Catalyzed Intramolecular Amination under Assistance of Oxalyl Amide5 Conclusion

scholarly journals Catalytic Benzolactamization Through Isonitrile Insertion Enabled 1,4-Palladium Shift

2021 ◽  
Author(s):  
Fulin Zhang ◽  
Ruihua Zhao ◽  
Lei Zhu ◽  
Yinghua Yu ◽  
Saihu Liao ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Heterocyclic Compounds ◽  
Bond Activation ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Mechanistic Studies ◽  
Carbon And Nitrogen ◽  
New Methods ◽  
Novel Approach ◽  
Bicyclic System

<b>Isoindolinone is a class of versatile <i>N</i>-heterocycles embedded in many bioactive molecules and natural products. The invention of new methods to synthesize these heterocyclic compounds with easily accessible chemicals is always attractive. Herein, a conceptually novel approach to access this bicyclic system via isonitrile insertion enabled 1,4-pallaidum shift is described. Compared with conventional isonitrile participated C-H bond activation, both carbon and nitrogen atoms in isonitrile moiety are engaged in new bond formation. Notably, two different isoindolinones can be obtained selectively by switching the bases employed. Mechanistic studies including DFT calculations have shed lights on the reaction mechanism and explained the selectivity led to different products. Moreover, the power of current benzolactamization is further demonstrated by providing concise routes to key intermediates of indoprofen, indobufen, aristolactams, lennoxamine and falipamil.</b>

C N bond formation in alicyclic and heterocyclic compounds by amine-modified nanoclay

2017 ◽  
Vol 1144 ◽  
pp. 58-65 ◽  
Author(s):  
Zohre Zarnegar ◽  
Roghayeh Alizadeh ◽  
Majid Ahmadzadeh ◽  
Javad Safari
Keyword(s):  
Heterocyclic Compounds ◽  
Bond Formation

A Review of Ruthenium-catalyzed C-N Bond Formation Reactions for the Synthesis of Five-membered N-heterocycles

2019 ◽  
Vol 23 (18) ◽  
pp. 1901-1944 ◽  
Author(s):  
Navjeet Kaur ◽  
Neha Ahlawat ◽  
Yamini Verma ◽  
Pooja Grewal ◽  
Pranshu Bhardwaj
Keyword(s):  
Heterocyclic Compounds ◽  
Functional Group ◽  
Bond Formation ◽  
Review Article ◽  
Transition Metal Catalysts ◽  
Heterocyclic Chemistry ◽  
Research Groups ◽  
Reaction Conditions ◽  
Alternative Pathways ◽  
Molecular Complexity

The field of heterocyclic chemistry has been revolutionized using transition metal catalysts in recent years. Various research groups have focused on the development of general protocols to achieve better functional group compatibilities and greater levels of molecular complexity under mild reaction conditions, using easily available starting substrates. The methodologies used earlier for their synthesis were less approachable to organic chemists because of their high cost, highly specified instrumentation and inconvenient methods. For both stereoselective and regioselective synthesis of five-membered nitrogen- containing heterocycles, cyclic reactions that are Ru-catalyzed have known to be very efficient. These methods have many advantages as compared to alternative pathways involved in the synthesis of heterocyclic compounds. In this review article, we concentrated on the synthesis of nitrogen-containing five-membered heterocycles in the presence of a ruthenium catalyst. This review mostly covers the literature published during the period from 1977-2019.

scholarly journals Iridium/Graphene Nanostructured Catalyst for the N-Alkylation of Amines to Synthesize Nitrogen-containing Derivatives and Heterocyclic Compounds

2021 ◽  
Author(s):  
Tsun-Ren Chen ◽  
Yu-Tung Chen ◽  
Yen-Hsing Lin ◽  
Hao-Chen Wang
Keyword(s):  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Bond Formation ◽  
Biologically Active ◽  
Secondary Alcohols ◽  
Nanostructured Catalyst ◽  
Synthetic Route ◽  
Tandem Catalysis ◽  
Intermolecular Cyclization ◽  
Privileged Structures

A facile iridium/graphene-catalyzed methodology providing an efficient synthetic route for C-N bond formation is reported. This catalyst can directly promote the formation of C-N bonds, without pre-activation steps, and without solvents, alkalis and other additives. This protocol provides a direct N -alkylation of amines using a variety of primary and secondary alcohols with good selectivity and excellent yields. Charmingly, the use of diols resulted in intermolecular cyclization of amines, and such products are privileged structures in biologically active compounds. Two examples illustrate the advantages of this catalyst in organic synthesis: the tandem catalysis to synthesize hydroxyine, and the intermolecular cyclyzation to synthesize cyclizine. Water is the only by-product, which makes this catalytic process sustainable and environmentally friendly.

scholarly journals Catalytic Benzolactamization Through Isonitrile Insertion Enabled 1,4-Palladium Shift

2021 ◽  
Author(s):  
Fulin Zhang ◽  
Ruihua Zhao ◽  
Lei Zhu ◽  
Yinghua Yu ◽  
Saihu Liao ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Heterocyclic Compounds ◽  
Bond Activation ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Mechanistic Studies ◽  
Carbon And Nitrogen ◽  
New Methods ◽  
Novel Approach ◽  
Bicyclic System

<b>Isoindolinone is a class of versatile <i>N</i>-heterocycles embedded in many bioactive molecules and natural products. The invention of new methods to synthesize these heterocyclic compounds with easily accessible chemicals is always attractive. Herein, a conceptually novel approach to access this bicyclic system via isonitrile insertion enabled 1,4-pallaidum shift is described. Compared with conventional isonitrile participated C-H bond activation, both carbon and nitrogen atoms in isonitrile moiety are engaged in new bond formation. Notably, two different isoindolinones can be obtained selectively by switching the bases employed. Mechanistic studies including DFT calculations have shed lights on the reaction mechanism and explained the selectivity led to different products. Moreover, the power of current benzolactamization is further demonstrated by providing concise routes to key intermediates of indoprofen, indobufen, aristolactams, lennoxamine and falipamil.</b>

Preparation of heterocyclic compounds via carbon-carbon bond formation catalyzed by an antibody

1996 ◽  
Vol 2 (1) ◽  
pp. 27-31 ◽  
Author(s):  
Tomoya Kitazume ◽  
Takashi Tsukamoto ◽  
Kouichi Murata ◽  
Koutaro Yoshimura
Keyword(s):  
Heterocyclic Compounds ◽  
Bond Formation ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Electrooxidative Cyclization of Hydroquinolyl Alcohols, Hydroquinolylamines, and Dimethyl Aminomalonates

2007 ◽  
Vol 60 (4) ◽  
pp. 236 ◽  
Author(s):  
Mitsuhiro Okimoto ◽  
Takashi Yoshida ◽  
Masayuki Hoshi ◽  
Kazuyuki Hattori ◽  
Masashi Komata ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Potassium Iodide ◽  
Sodium Methoxide ◽  
Heterocyclic Compounds ◽  
Bond Formation ◽  
Sodium Cyanide ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Several hydroquinolyl alcohols and amines were electrochemically oxidized in methanol in the presence of sodium methoxide and potassium iodide to afford the corresponding intramolecular cyclization products. Furthermore, several amino malonates were electrochemically oxidized to yield the corresponding heterocyclic compounds through an intramolecular carbon–carbon bond formation in the presence of sodium cyanide in methanol.

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