An Improved Synthesis of Urea Derivatives from N-Acylbenzotriazole via Curtius Rearrangement

Synthesis ◽  
2019 ◽  
Vol 51 (18) ◽  
pp. 3443-3450 ◽  
Author(s):  
Anoop S. Singh ◽  
Anand K. Agrahari ◽  
Sumit K. Singh ◽  
Mangal S. Yadav ◽  
Vinod K. Tiwari
Keyword(s):  
Reaction Time ◽  
Column Chromatography ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Urea Derivatives ◽  
Curtius Rearrangement ◽  
Short Reaction Time ◽  
Metal Free ◽  
Salient Features

The good leaving tendency of the benzotriazole moiety has been exploited for the synthesis of symmetric, unsymmetric, N-acyl, and cyclic ureas in good yields from N-acylbenzotriazoles by treating the latter with various amines in the presence of TMSN3/Et3N in a sealed tube. The salient features of the devised protocol includes the high-yield, mild, metal-free, one-pot reaction conditions, and short reaction time. Furthermore, in many cases, no column chromatography is required for the purification.

scholarly journals Microwave Assisted One Pot Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives using [Emim]OH Ionic Liquid as Novel Catalyst

2019 ◽  
Vol 31 (4) ◽  
pp. 829-833
Author(s):  
D.S. Bhagat ◽  
S.G. Pande ◽  
M.V. Katariya ◽  
R.P. Pawar ◽  
P.S. Kendrekar
Keyword(s):  
Ionic Liquid ◽  
Reaction Time ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
Aryl Aldehydes ◽  
Microwave Assisted ◽  
Novel Catalyst ◽  
Work Up

One-pot efficient protocol to the synthesis of 2-amino-5-oxo-4,5-dihydropyrano(3,2-c)chromene-3-carbonitrile derivatives via condensation of various aryl aldehydes, dicyanomethane and 4-hydroxycoumarin in presence of Emim hydroxide as an excellent homogeneous liquid catalyst. The key advantages of this methodology are mild reaction conditions, novel catalyst, short reaction time, eco-friendly, easy work-up procedure and high yield of isolation of derivatives.

A One-pot Multi-component Synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates Catalysed by Oxalic Acid Dihydrate

2013 ◽  
Vol 37 (1) ◽  
pp. 40-42 ◽  
Author(s):  
Seyed Sajad Sajadikhah ◽  
Nourallah Hazeri ◽  
Malek Taher Maghsoodlou ◽  
Mostafa Sayyed Habibi-Khorassani ◽  
Khatereh Khandan-Barani
Keyword(s):  
Reaction Time ◽  
Oxalic Acid ◽  
Column Chromatography ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
Oxalic Acid Dihydrate ◽  
Dialkyl Acetylenedicarboxylates ◽  
High Yields ◽  
Work Up

A simple synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates via one-pot multi-component reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of oxalic acid dihydrate (20 mol%) as catalyst in methanol is described. This homogeneous catalytic procedure offers advantages including mild reaction conditions, good to high yields, short reaction time, simple and readily available starting materials, easy work-up and there is no need for column chromatography.

scholarly journals One-Pot Green Synthesis of Some Novel N-Substituted 5-Amino-1,3,4- Thiadiazole Derivatives

2020 ◽  
Vol 17 (7) ◽  
pp. 517-522
Author(s):  
Azizollah Habibi ◽  
Sahar Khosravi ◽  
Seyyed M. Shahcheragh ◽  
Mohd B. Abdul Rahman
Keyword(s):  
Reaction Time ◽  
Green Synthesis ◽  
Spectroscopic Data ◽  
Barbituric Acid ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Three Component Reaction ◽  
Environmentally Safe ◽  
Thiadiazole Derivatives

In the current study, a green, one-pot, three-component reaction was performed to prepare novel N-substituted 5-amino-1,3,4-thiadiazole derivatives. The thiadiazoles were obtained from the reaction of a ketene S,S-acetal of Meldrum’s acid or barbituric acid (as key intermediates), hydrazine, and isothiocyanate. The key advantages of this manner include environmentally safe reactions, high yield, appropriate reaction time, simple reaction conditions, and use of a green reaction solvent. The structure of thiadiazoles was determined based on the spectroscopic data.

scholarly journals Fe3O4@chitosan-tannic acid bionanocomposite as a novel nanocatalyst for the synthesis of pyranopyrazoles

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Maryam Kamalzare ◽  
Mohammad Reza Ahghari ◽  
Mohammad Bayat ◽  
Ali Maleki
Keyword(s):  
Reaction Time ◽  
Tannic Acid ◽  
High Performance ◽  
Catalytic Performance ◽  
Natural Material ◽  
Magnetic Nanocatalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
High Yields

AbstractRecently magnetic nanocatalyst has attracted considerable attention because of its unique properties, including high performance, easy separation from the reaction mixture, and recyclability. In this study, a novel magnetic bionanocomposite was synthesized with chitosan and tannic acid as a natural material. The synthesized bionanocatalyst was characterized by essential analysis. Fe3O4@chitosan-tannic acid as a heterogeneous nanocatalyst was successfully applied to synthesize pyranopyrazole and its derivatives by a one-pot four-component reaction of malononitrile, ethyl acetoacetate, hydrazine hydrate, and various aromatic aldehyde. At the end of the reaction, the nanocatalyst was separated from the reaction mixture and was reused several times with no significant decrease in its catalytic performance. Simple purification of products, the ability for recovering and reusing the nanocatalyst, eco-friendliness, high yields of pure products, mild reaction conditions, short reaction time, non-toxicity, economically affordable are some of the advantages of using the fabricated nanocatalyst in the synthesis of pyranopyrazole.

scholarly journals Pentafluoropropionic Acid: An Efficient and Metal-Free Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives

2014 ◽  
Vol 2014 ◽  
pp. 1-5 ◽  
Author(s):  
Naser Montazeri ◽  
Taghva Noghani ◽  
Mona Ghorchibeigy ◽  
Rozita Zoghi
Keyword(s):  
Reaction Time ◽  
Aromatic Aldehyde ◽  
One Pot ◽  
Short Reaction Time ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
The One ◽  
High Yields

Pentafluoropropionic acid (PFPA) efficiently catalyzes the one-pot, three-component reaction of aromatic aldehyde, malononitrile, and dimedone to yield tetrahydrobenzo[b]pyran derivatives in high yields. This method is of great value because of its easy processing, short reaction time, environmentally, and high yields.

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 Highly Efficient Recyclable Sol Gel Polymer Catalyzed One Pot Difunctionalization of Alkynes

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1879
Author(s):  
Justin Domena ◽  
Carlos Chong ◽  
Qiaxian Johnson ◽  
Bhanu Chauhan ◽  
Yalan Xing
Keyword(s):  
Reaction Time ◽  
Room Temperature ◽  
Functional Group ◽  
Sol Gel ◽  
One Pot ◽  
Short Reaction Time ◽  
Metal Free ◽  
Highly Efficient

Amino-bridged gel polymer P1 was discovered to catalyze alkyne halo-functionalization in excellent yields, regioselectivity, functional group compatibility, and recyclability. We have observed that both aromatic and aliphatic alkynes can be converted to α,α-dihalogenated ketones in the presence of polymer P1 under metal-free conditions at room temperature within a short reaction time.

Phosphomolybdic Acid (PMA)-catalyzed One-pot Synthesis of 2,3- Dihydroquinazolines

2019 ◽  
Vol 16 (8) ◽  
pp. 683-687
Author(s):  
Chuanhuan Chen ◽  
A. Xuejiao ◽  
Xia Li ◽  
Guoli Huang ◽  
Bo Liu
Keyword(s):  
Reaction Time ◽  
Present Method ◽  
Room Temperature ◽  
Phosphomolybdic Acid ◽  
New Method ◽  
High Yield ◽  
One Pot ◽  
Short Reaction Time ◽  
One Pot Synthesis

We have developed a new method for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones in good to excellent yields via phosphomolybdic acid (PMA)-catalyzed cyclocondensation of 2- aminobenzamides with aldehydes or ketones in N,N-dimethylformamide (DMF) at room temperature. The present method proves to be efficient in terms of short reaction time, high yield, simple workup and easy purification.

Nucleophilic Acylation with Aromatic Aldehydes to 2 Bromoacetonitrile: An Umpolung Strategy for the Synthesis of Active Methylene Compounds

2020 ◽  
Vol 17 (7) ◽  
pp. 518-524
Author(s):  
Shailesh Singh ◽  
Jyoti Tiwari ◽  
Deepali Jaiswal ◽  
Amit Kumar Sharma ◽  
Jaya Singh ◽  
...  
Keyword(s):  
Reaction Time ◽  
Ambient Temperature ◽  
Aromatic Aldehydes ◽  
Product Formation ◽  
One Pot ◽  
Short Reaction Time ◽  
Salient Features ◽  
High Yields ◽  
Operational Simplicity ◽  
Nucleophilic Acylation

Background: A novel one-pot N-heterocyclic carbene (NHC)-catalysed acylation of 2- bromoacetonitrile with aromatic aldehydes is reported. The protocol involves carbonyl umpolung reactivity of aldehydes in which the carbonyl carbon attacks nucleophilically (as d1 nucleophile) on the electrophilic terminal of 2-bromoacetonitrile to afford 3-aryl-3-oxopropanenitrile. The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no by-product formation and high yields. Materials and Methods: A flame-dried round bottom flask was charged with Imidazolium salts (3a) (0.20 mmol). Aldehyde 1a (1.0 mmol), 2-bromoacetonitrile 2 (1.0 mmol), and THF / t-BuOH 5 mL; 10:1) were added at positive nitrogen pressure followed by the addition of DBU (0.15 mmol) through stirring. The resulting yellow- orange solution was stirred at room temperature for 5-6 h. After completion of the reaction (TLC monitored), the reaction mixture was concentrated under reduced pressure. The product was purified using hexane / EtOAc (10:1) as an eluent to provide analytically pure compound 4a. Physical data of representative compounds and the NMR spectroscopic data are in agreement with the literature value. Results and Discussion: The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no by-product formation and high yields. Conclusion: To sum up, we have developed a convenient, efficient and one-pot route for 3-oxo-3- phenylpropanenitrile synthesis from NHC promoted direct nucleophilic acylation of aromatic aldehydes using 2- bromoacetonitrile. This method provided a wide range of products and good yields. To best of our knowledge, this is the new report for the synthesis of 3-oxo-3-phenylpropanenitrile through NHC promoted nucleophilic acylation of aromatic aldehyde.

scholarly journals Microwave-Induced Montmorillonite-Mediated Facile Synthesis of Enamines

2019 ◽  
Vol 32 (2) ◽  
pp. 249-254
Author(s):  
Ram Naresh Yadav ◽  
Indrani Banik ◽  
Ashok Kumar Srivastava ◽  
Katherine Ramos ◽  
Bimal Krishna Banik
Keyword(s):  
Reaction Time ◽  
Carbonyl Compounds ◽  
Montmorillonite Clay ◽  
Secondary Amines ◽  
High Yield ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
Cyclic Amines

Montmorillonite clay-mediated simple and high yielding protocol for the synthesis of various enamines with secondary amines and ketones is developed under microwave condition. This protocol is very convenient to accesses the enamines from cyclic amines with various carbonyl compounds in high yield under mild reaction conditions with short reaction time.

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