Green synthesis of benzoimidazopyrimidine, benzimidazoloquinazolinone, triazolopyrimidine and triazoloquinazolinone derivatives catalyzed by oxalic acid dihydrate

2021 ◽  
Vol 18 ◽  
Author(s):  
Seyed Sajad Sajadikhah ◽  
Bagher Liravi-Deylami
Keyword(s):  
Oxalic Acid ◽  
Green Synthesis ◽  
Column Chromatography ◽  
Catalytic Amount ◽  
Atom Economy ◽  
One Pot ◽  
Oxalic Acid Dihydrate ◽  
Metal Free ◽  
Solvent Free Conditions ◽  
Simple Filtration

: Benzoimidazopyrimidine, benzimidazoloquinazolinone, triazolopyrimidine, and triazoloquinazolinone derivatives were synthesized via a one-pot multi-component reaction in the presence of a catalytic amount of oxalic acid dihydrate. The reactions were performed in the mixture of EtOH: H2O or under solvent-free conditions as green media. The advantageous features of these methodologies are inexpensive starting materials and catalyst, high atom economy and good yields, and metal-free synthesis. Moreover, all the products were obtained by simple filtration with no need for column chromatography or tedious separation procedures, which is very important in terms of reducing environmental pollutions.

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 and Metal-Free Synthesis of 3-Arylated 4-Nitrophenols via Polyfunctionalized Cyclohexanones from β-Nitrostyrenes

2020 ◽  
Author(s):  
Haruyasu Asahara ◽  
Minami Hiraishi ◽  
Nagatoshi Nishiwaki
Keyword(s):  
Dimethyl Sulfoxide ◽  
Catalytic Amount ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Metal Free ◽  
Diels Alder Reaction ◽  
Thienyl Group ◽  
Danishefsky's Diene

β-Nitrostyrenes underwent the Diels-Alder reaction with Danishefsky’s diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated 5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated 4-nitrophenols. The reaction of nitrostyrenes with Danishefsky’s diene could be conducted in one-pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group such as a thienyl group could be introduced into the nitrophenol framework.

scholarly journals One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

2020 ◽  
Vol 16 ◽  
pp. 1830-1836
Author(s):  
Haruyasu Asahara ◽  
Minami Hiraishi ◽  
Nagatoshi Nishiwaki
Keyword(s):  
Dimethyl Sulfoxide ◽  
Catalytic Amount ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Metal Free ◽  
Diels Alder Reaction ◽  
Thienyl Group ◽  
Danishefsky's Diene

β-Nitrostyrenes underwent a Diels–Alder reaction with Danishefsky’s diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated-5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated-4-nitrophenols. The reaction of nitrostyrenes with Danishefsky’s diene could be conducted in one pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group, e.g., a thienyl group could be introduced into the nitrophenol framework.

A facile and highly convergent approach to thiazolo[3,2-a]pyridines via one-pot multicomponent domino reaction under metal-free and solvent-free conditions

Tetrahedron ◽  
2015 ◽  
Vol 71 (21) ◽  
pp. 3422-3427 ◽  
Author(s):  
Anugula Nagaraju ◽  
B. Janaki Ramulu ◽  
Gaurav Shukla ◽  
Abhijeet Srivastava ◽  
Girijesh Kumar Verma ◽  
...  
Keyword(s):  
Solvent Free ◽  
Domino Reaction ◽  
One Pot ◽  
Metal Free ◽  
Solvent Free Conditions ◽  
Convergent Approach

ChemInform Abstract: A One-Pot Multi-Component Synthesis of N-Aryl-3-aminodihydropyrrol-2-one-4-carboxylates Catalyzed by Oxalic Acid Dihydrate.

ChemInform ◽  
2013 ◽  
Vol 44 (28) ◽  
pp. no-no
Author(s):  
Seyed Sajad Sajadikhah ◽  
Nourallah Hazeri ◽  
Malek Taher Maghsoodlou ◽  
Sayyed Mostafa Habibi-Khorassani ◽  
Khatereh Khandan-Barani
Keyword(s):  
Oxalic Acid ◽  
One Pot ◽  
Oxalic Acid Dihydrate

Glutamic Acid as an Efficient and Green Catalyst for the One-Pot Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles under Thermal, Solvent-Free Conditions

2017 ◽  
Vol 41 (11) ◽  
pp. 673-675 ◽  
Author(s):  
Fahimeh Khazaee Feizabad ◽  
Khatereh Khandan-Barani ◽  
Alireza Hassanabadi
Keyword(s):  
Glutamic Acid ◽  
Reaction Times ◽  
Catalytic Amount ◽  
Solvent Free ◽  
One Pot ◽  
Green Catalyst ◽  
Aryl Aldehydes ◽  
Solvent Free Conditions ◽  
The One ◽  
Tetrasubstituted Imidazoles

A high-yielding synthesis of 1,2,4,5-tetrasubstituted imidazoles is described, involving the reaction of 1,2-dicarbonyl compounds, aryl aldehydes, amines and ammonium acetate in the presence of a catalytic amount of glutamic acid under thermal, solvent-free conditions. The salient features of this protocol are aerobic conditions, a non-hazardous green catalyst, short reaction times and mild reaction conditions.

ChemInform Abstract: One-Pot Five-Component Synthesis of Highly Functionalized Piperidines Using Oxalic Acid Dihydrate as a Homogenous Catalyst.

ChemInform ◽  
2012 ◽  
Vol 43 (40) ◽  
pp. no-no
Author(s):  
Seyed Sajad Sajadikhah ◽  
Malek Taher Maghsoodlou ◽  
Nourallah Hazeri ◽  
Sayyed Mostafa Habibi-Khorassani ◽  
Anthony C. Willis
Keyword(s):  
Oxalic Acid ◽  
One Pot ◽  
Oxalic Acid Dihydrate ◽  
Homogenous Catalyst

ChemInform Abstract: Oxalic Acid Dihydrate: A Reusable and Cost-Effective Catalyst for the Synthesis of Bis(indolyl)methanes under Solvent-Free Conditions.

ChemInform ◽  
2008 ◽  
Vol 39 (51) ◽  
Author(s):  
Minoo Dabiri ◽  
Mostafa Baghbanzadeh ◽  
Seyedeh C. Azimi ◽  
Shaghayegh Ahmadzadeh-Asl ◽  
Reza R. Ardestani
Keyword(s):  
Oxalic Acid ◽  
Cost Effective ◽  
Solvent Free ◽  
Oxalic Acid Dihydrate ◽  
Effective Catalyst ◽  
Solvent Free Conditions

scholarly journals Phospho sulfonic acid: A novel and efficient solid acid catalyst for the one-pot preparation of 2H-indazolo[2,1-b]-phthalazine-triones

2013 ◽  
Vol 78 (4) ◽  
pp. 469-476 ◽  
Author(s):  
Reza Kiasat ◽  
Arash Mouradezadegun ◽  
Jafar Saghanezhad
Keyword(s):  
Sulfonic Acid ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Catalytic Amount ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
The One ◽  
Short Time

The efficient one-pot condensation of aldehyde, dimedone, and phthalhydrazide has been achieved in the presence of a catalytic amount of phospho sulfonic acid as a novel environmentally benign heterogeneous solid acid under solvent-free conditions. A diversified 2H-indazolo[1,2-b]phthalazinetrione derivatives were prepared in good to excellent yields in short time. The economical factors (time, cost, waste etc.) for this three-component reaction hold promise for the future of organic synthesis.

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