scholarly journals Synthesis of β-Amino Carbonyl Compounds via the Iodine-Alumina Catalyzed Three-Component Coupling Reaction under Microwave Irradiation

2011 ◽  
Vol 2011 ◽  
pp. 1-7 ◽  
Author(s):  
Mantu Rajbangshi ◽  
Md. Rumum Rohman ◽  
Icydora Kharkongor ◽  
Hormi Mecadon ◽  
Bekington Myrboh
Keyword(s):  
Reaction Time ◽  
Microwave Irradiation ◽  
Carbonyl Compounds ◽  
Aromatic Amines ◽  
Coupling Reaction ◽  
Environmentally Friendly ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Key Features ◽  
Operational Simplicity

Iodine-alumina was employed as a catalyst in the coupling reactions of aldehydes, enolizable ketones, or 1,3-dicarbonyls with methyl carbamate or aromatic amines under microwave irradiation to afford β-amino carbonyl compounds in good-to-excellent yields. The key features of this environmentally friendly methodology are its operational simplicity, mild reaction conditions, and less reaction time.

An Unprecedented Cyano-Induced Sodium Nitrite-Catalyzed C(sp3)-H and C(sp2)-H Coupling Reaction

2018 ◽  
Vol 15 (7) ◽  
pp. 989-994 ◽  
Author(s):  
Ling Li ◽  
Bo Su ◽  
Yuxiu Liu ◽  
Qingmin Wang
Keyword(s):  
Sodium Nitrite ◽  
Oxidative Coupling ◽  
High Resolution Mass Spectrometry ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Oxidative Coupling Reaction ◽  
Oxidative Coupling Reactions

Aim and Objective: During the investigation of sodium nitrite-catalyzed oxidative coupling reaction of aryls, an unprecedented C(sp2)-H and C(sp3)-H coupling of substituted 2-aryl acetonitrile was found. Materials and Methods: The structure of the coupled product was confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry (HRMS), and comparison of its derivatives with known compounds. The effects of methoxy group in the benzene ring on the reaction were evaluated. Results: The optimized reaction conditions are summarized as follows: CF3SO3H/substrate = 1.5 equiv., NaNO2/substrate = 0.3 equiv., CH3CN as solvent. 2-(4-Methoxyphenyl)acetonitrile and 2-(3,4,5- trimethoxyphenyl)acetonitrile could also generate C(sp2)-H and C(sp3)-H coupling. The coupling reaction occurred as a typical radial mechanism. Conclusion: An unprecedented cyano-induced, NaNO2-catalyzed oxidative C(sp3)-H and C(sp2)-H coupling was reported. The reaction proceeded under very mild conditions, using O2 in the air as terminal oxidant. The unique oxidative manner might provide more inspiration for the development of intriguing oxidative coupling reactions.

Preparation of aromatic amines by copper-catalyzed coupling of boronic acids with aqueous ammonia

2010 ◽  
Vol 88 (9) ◽  
pp. 964-968 ◽  
Author(s):  
Zhaoqiong Jiang ◽  
Zhiqing Wu ◽  
Lixia Wang ◽  
Di Wu ◽  
Xiangge Zhou
Keyword(s):  
Aromatic Amines ◽  
Aqueous Ammonia ◽  
Environmentally Friendly ◽  
Boronic Acids ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Primary Aromatic Amines

A simple, highly efficient, and environmentally friendly protocol for the synthesis of primary aromatic amines by catalytic coupling of aromatic boronic acids with aqueous ammonia has been developed by using commercial and inexpensive CuSO4·5H2O as catalyst without addition of other solvents under mild reaction conditions.

scholarly journals Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

2018 ◽  
Vol 14 ◽  
pp. 1871-1884 ◽  
Author(s):  
Siva Sankar Murthy Bandaru ◽  
Darinka Dzubiel ◽  
Heiko Ihmels ◽  
Mohebodin Karbasiyoun ◽  
Mohamed M A Mahmoud ◽  
...  
Keyword(s):  
Emission Intensity ◽  
Binding Constants ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Reaction Conditions ◽  
Quadruplex Dna ◽  
Cross Coupling Reactions ◽  
Sonogashira Coupling Reaction

9-Arylbenzo[b]quinolizinium derivatives were prepared with base-free Suzuki–Miyaura coupling reactions between benzo[b]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[b]quinolizinium and the arylalkyne derivatives yielded four novel 9-(arylethynyl)benzo[b]quinolizinium derivatives under relatively mild reaction conditions. The 9-(N,N-dimethylaminophenylethynyl)benzo[b]quinolizinium is only very weakly emitting, but the emission intensity increases by a factor >200 upon protonation, so that this derivative may operate as pH-sensitive light-up probe. Photometric and fluorimetric titrations of duplex and quadruplex DNA to 9-(arylethynyl)benzo[b]quinolizinium derivatives revealed a significant binding affinity of these compounds towards both DNA forms with binding constants ofKb= 0.2–2.2 × 105M−1.

scholarly journals Microwave Assisted Synthesis of 1,5-Benzothiazepines Using Greener Reaction Medium

2019 ◽  
Vol 31 (5) ◽  
pp. 993-996 ◽  
Author(s):  
Sanjay S. Kotalwar ◽  
Amol D. Kale ◽  
Ram B. Kohire ◽  
Vasant B. Jagrut
Keyword(s):  
Reaction Time ◽  
Microwave Irradiation ◽  
Reaction Medium ◽  
Microwave Assisted Synthesis ◽  
Reaction Conditions ◽  
Renewable Sources ◽  
Microwave Assisted ◽  
High Yields

An efficient and eco-friendly synthesis of 1,5-benzothiazepines has been developed by the reaction of various 2-propen-1-ones with 2-aminothiophenol using microwave irradiation in greener reaction medium, glycerol. The clean reaction conditions, shorter reaction time, high yields and non-toxic, biodegradable reaction medium manufactured from renewable sources are unique features of this method.

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

DMAP-catalyzed Efficient and Convenient Approach for the Synthesis of 3,3′-(Arylmethylene)bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives

2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110458
Author(s):  
Le Nhat Thuy Giang ◽  
Dang Thi Tuyet Anh ◽  
Hoang Thi Phuong ◽  
Nguyen Ha Thanh ◽  
Nguyen Thi Quynh Giang ◽  
...  
Keyword(s):  
Reaction Time ◽  
Microwave Irradiation ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Basic Catalyst ◽  
Reaction Conditions ◽  
Efficient Procedure ◽  
Short Reaction Time ◽  
Convenient Approach ◽  
First Time

For the first time the 4-dimethylaminopyridine (DMAP) catalyzed straightforward and efficient procedure has been developed for the synthesis of 3,3′-(arylmethylene) bis(2-hydroxynaphthalene-1,4-dione) derivatives starting from lawsone (2-hydroxy-1,4-naphthoquinone) and a variety of (hetero)aromatic aldehydes in ethanol under microwave irradiation. Three of nine synthesized compounds are new. This method provides notable advantages over existing procedures including use of non-traditional basic catalyst and environmentally benign solvent, mild reaction conditions, excellent yields, short reaction time and simple workup.

scholarly journals Anthranilic acids from isatin: an efficient, versatile and environmentally friendly method

2015 ◽  
Vol 87 (3) ◽  
pp. 1525-1529 ◽  
Author(s):  
GABRIEL F. RIO ◽  
BÁRBARA V. SILVA ◽  
SABRINA T. MARTINEZ ◽  
ANGELO C. PINTO
Keyword(s):  
Reaction Time ◽  
Nitrogen Atom ◽  
Aromatic Ring ◽  
Room Temperature ◽  
Environmentally Friendly ◽  
Reaction Conditions ◽  
Anthranilic Acids ◽  
Environmentally Friendly Method

This paper describes the preparation of a series of 16 anthranilic acids in yields ranging from 51 to 97%, by treating the isatins with NaOH and H2O2. Independently of the nature of the substituent on the aromatic ring, the reactions were complete in 15 min at room temperature, whereas those of isatins containing a substituent on the nitrogen atom required longer reaction time for completion (45 min) under the same reaction conditions.

Molecular iodine-catalysed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or sulfonamides

2009 ◽  
Vol 2009 (10) ◽  
pp. 638-641 ◽  
Author(s):  
Xufeng Lin ◽  
Jun Wang ◽  
Fangxi Xu ◽  
Yanguang Wang
Keyword(s):  
Reaction Time ◽  
Efficient Method ◽  
Bond Formation ◽  
Molecular Iodine ◽  
Allylic Alcohols ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
Metal Free ◽  
Amidation Reaction ◽  
Operational Simplicity

A highly efficient method for the C–N bond formation via 2 mol% of molecular iodine-catalysed amidation reaction of benzylic and allylic alcohols with carboxamides or sulfonamides in MeCN is described, giving the corresponding substituted amides and allylic amides in moderate to excellent yields. The significan features of the procedure include mild and metal-free reaction conditions, operational simplicity, inexpensive reagents, short reaction time, and good yields.

scholarly journals The in situ generation and reactive quench of diazonium compounds in the synthesis of azo compounds in microreactors

2016 ◽  
Vol 12 ◽  
pp. 1987-2004 ◽  
Author(s):  
Faith M Akwi ◽  
Paul Watts
Keyword(s):  
Continuous Flow ◽  
Coupling Reaction ◽  
Azo Compounds ◽  
Coupling Reactions ◽  
Azo Coupling ◽  
Reaction Conditions ◽  
Flow Rates ◽  
Flow Synthesis ◽  
Optimum Flow

In this paper, a micro-fluidic optimized process for the continuous flow synthesis of azo compounds is presented. The continuous flow synthesis of Sudan II azo dye was used as a model reaction for the study. At found optimal azo coupling reaction temperature and pH an investigation of the optimum flow rates of the reactants for the diazotization and azo coupling reactions in Little Things Factory-MS microreactors was performed. A conversion of 98% was achieved in approximately 2.4 minutes and a small library of azo compounds was thus generated under these reaction conditions from couplers with aminated or hydroxylated aromatic systems. The scaled up synthesis of these compounds in PTFE tubing (i.d. 1.5 mm) was also investigated, where good reaction conversions ranging between 66–91% were attained.

scholarly journals CuI-Catalyzed Coupling Reactions of 4-Iodopyrazoles and Alcohols: Application toward Withasomnine and Homologs

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3370
Author(s):  
Yoshihide Usami ◽  
Yumika Kubo ◽  
Toshiki Takagaki ◽  
Nao Kuroiwa ◽  
Jun Ono ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Present Method ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Optimal Reaction

The direct 4-alkoxylation of 4-iodo-1H-pyrazoles with alcohols was achieved by a CuI-catalyzed coupling protocol. The optimal reaction conditions employed excess alcohol and potassium t-butoxide (2 equiv) in the presence of CuI (20 mol%) and 3,4,7,8-tetramethyl-1,10-phenanthroline (20 mol%) at 130 °C for 1 h under microwave irradiation. The present method was efficiently applied to the synthesis of withasomnine and its six- and seven-membered cyclic homologs.

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