scholarly journals Umpolung of Indoles: Triflic Acid-Mediated C3-Regioselective Hy-droarylation of N-H Indoles

2022 ◽  
Author(s):  
Nazarii Sabat ◽  
Weiping Zhou ◽  
Vincent Gandon ◽  
Xavier Guinchard ◽  
Guillaume VINCENT
Keyword(s):  
Room Temperature ◽  
Atom Economy ◽  
Triflic Acid ◽  
Straightforward Manner ◽  
Biologically Relevant ◽  
Acetyl Group ◽  
High Yields

The direct dearomative addition of arenes to the C3-position of unprotected indoles is reported under operationally simple conditions with triflic acid at room temperature. The present regioselective hydroarylation is a straightforward manner to gen-erate an electrophilic indole at the C3-position without the need to introduce a deactivating acetyl group on the indolic nitrogen as in previously reported strategies. This atom economy method delivers biologically relevant 3-aryl indolines and 3,3-spiroindolines in high yields and regioselectivities from both intra and intermolecular processes.

scholarly journals Zn(L-proline)2: An efficient and reusable organocatalyst for the synthesis of polyfunctionally substituted pyrans and 2-amino-4-aryl-8-oxo-4,8-dihydropyrano[3,2-b]pyran derivatives

2019 ◽  
Vol 10 (2) ◽  
pp. 166-170 ◽  
Author(s):  
Fatma Ahmed Abo Elsoud ◽  
Mohamed Abd-Elmonem ◽  
Mohamed Abo Elsebaa ◽  
Kamal Usef Sadek
Keyword(s):  
Kojic Acid ◽  
Aromatic Aldehydes ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Short Reaction Time ◽  
Biologically Relevant ◽  
Three Component Reaction ◽  
High Yields ◽  
Organometallic Catalyst ◽  
Work Up

Efficient synthesis of non-annulated 2-amino-4H-pyrans and 2-amino-8-oxo-4,8-dihydropyrano[3,2-b]pyran derivatives, which are biologically relevant heterocycles is achieved, utilizing a domino three-component reaction of ethyl acetoacetate or kojic acid with aromatic aldehydes and malononitrile catalyzed by Zn(L-proline)2 as reusable organometallic catalyst. The process exhibits high atom economy, short reaction time, simple work up, high yields and environmentally friendly nature. Excellent yields of the targeted molecules have been obtained.

scholarly journals Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

2019 ◽  
Vol 15 ◽  
pp. 874-880
Author(s):  
Razieh Navari ◽  
Saeed Balalaie ◽  
Saber Mehrparvar ◽  
Fatemeh Darvish ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Room Temperature ◽  
High Selectivity ◽  
Domino Reaction ◽  
Primary Amines ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Three Component Reaction ◽  
High Yields

An efficient approach for the synthesis of pyrazolopyridines containing the aminochromane motif through a base-catalyzed cyclization reaction is reported. The synthesis was carried out through a three-component reaction of (arylhydrazono)methyl-4H-chromen-4-one, malononitrile, primary amines in the presence of Et3N at room temperature. However, carrying out the reaction under the same conditions without base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach.

scholarly journals Catalyst-Free Polymerization with 100% Atom Economy: Facile Synthesis of Polysulfonates with Multifunctionalities

2020 ◽  
Author(s):  
XIAOLIN LIU ◽  
Xin Liang ◽  
YUBING HU ◽  
Qing Qu ◽  
Dongming Liu ◽  
...  
Keyword(s):  
Refractive Index ◽  
Antibacterial Activity ◽  
Room Temperature ◽  
High Refractive Index ◽  
Atom Economy ◽  
Facile Synthesis ◽  
Spontaneous Polymerization ◽  
Catalyst Free ◽  
High Yields ◽  
Post Functionalization

Catalyst-free spontaneous polymerization for the synthesis of halogen-rich polysulfonates at room temperature in air with 100% atom economy in high yields was developed. The resulting polymers possess various properties, including post-functionalization, extraordinarily high refractive index, visible photodegradation, photoacid generation, multi-color and 3D fluorescent photopatterning, and practical broad-spectrum antibacterial activity.

scholarly journals Catalyst-Free Polymerization with 100% Atom Economy: Facile Synthesis of Polysulfonates with Multifunctionalities

2020 ◽  
Author(s):  
XIAOLIN LIU ◽  
Xin Liang ◽  
YUBING HU ◽  
Qing Qu ◽  
Dongming Liu ◽  
...  
Keyword(s):  
Refractive Index ◽  
Antibacterial Activity ◽  
Room Temperature ◽  
High Refractive Index ◽  
Atom Economy ◽  
Facile Synthesis ◽  
Spontaneous Polymerization ◽  
Catalyst Free ◽  
High Yields ◽  
Post Functionalization

Catalyst-free spontaneous polymerization for the synthesis of halogen-rich polysulfonates at room temperature in air with 100% atom economy in high yields was developed. The resulting polymers possess various properties, including post-functionalization, extraordinarily high refractive index, visible photodegradation, photoacid generation, multi-color and 3D fluorescent photopatterning, and practical broad-spectrum antibacterial activity.

scholarly journals Chemoselective aza-Michael addition of indoles to 2-aroyl-1,3-diarylenones

2019 ◽  
Vol 44 (1-2) ◽  
pp. 97-103
Author(s):  
Zheng Li ◽  
Aizhen Yang ◽  
Xiaolong Ma ◽  
Zhenrong Liu
Keyword(s):  
Transition Metal ◽  
Michael Addition ◽  
Potassium Hydroxide ◽  
Room Temperature ◽  
Transition Metal Catalysts ◽  
Atom Economy ◽  
Mild Conditions ◽  
High Yields ◽  
Work Up ◽  
Aryl Methyl

A total of 20 examples of 2-[(1 H-indol-1-yl)(aryl)methyl]-1,3-diphenylpropane-1,3-diones were efficiently synthesized by the aza-Michael addition at the N1 position of indoles with 2-aroyl-1,3-diarylenones at room temperature in the presence of potassium hydroxide. The salient features of this protocol are no transition-metal catalysts, mild conditions, high chemoselectivity, high atom economy, high yields, and a simple work-up procedure.

scholarly journals Efficient and Facile One-Pot Synthesis of Novel Benzimidazoles using Rice Husk

2020 ◽  
pp. 27-32
Author(s):  
Suman Suman ◽  
Rajvir Singh ◽  
Susheel Gulati ◽  
Suprita Suprita
Keyword(s):  
Rice Husk ◽  
Room Temperature ◽  
Rice Husk Ash ◽  
Atom Economy ◽  
One Pot ◽  
Green Catalyst ◽  
Filter Pump ◽  
High Yields ◽  
Work Up ◽  
Layer Chromatography

New and facile one-pot approach for the synthesis of substituted benzimidazoles from the reaction of substituted benzaldehyde and o-phenylenediamine room temperature using Rice Husk Ash: CaCl2 (RHA:CaCl2) as a green catalyst was presented in the paper. After the completion of the reaction, the reaction mixture was poured into ice-coldwater with stirring, and the precipitated product was filtered using the filter pump. The crude product was then recrystallized from ethanol to give analytically pure samples in good to excellent yield. The purity of compounds were characterized by melting point and thin-layer chromatography. The synthesized compounds were characterized by using 1HNMR and FTIR spectral techniques.Metal-free, short reaction time, high yields, mild reaction condition, simple work-up, high atom economy, cost-effectiveness, and no need for column purification are some beauties of this methodology.

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

scholarly journals Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

2013 ◽  
Vol 9 ◽  
pp. 8-14 ◽  
Author(s):  
Yan Sun ◽  
Jing Sun ◽  
Chao-Guo Yan
Keyword(s):  
Acetic Acid ◽  
Reaction Mechanism ◽  
Room Temperature ◽  
The Other ◽  
Other Hand ◽  
Three Component Reaction ◽  
High Yields

A fast and convenient protocol for the synthesis of novel spiro[dihydropyridine-oxindole] derivatives in satisfactory yields was developed by the three-component reactions of arylamine, isatin and cyclopentane-1,3-dione in acetic acid at room temperature. On the other hand the condensation of isatin with two equivalents of cyclopentane-1,3-dione gave 3,3-bis(2-hydroxy-5-oxo-cyclopent-1-enyl)oxindole in high yields. The reaction mechanism and substrate scope of this novel reaction is briefly discussed.

Boron Trifluoride-assisted Reactions of 1-Benzothiophen-3(2H)-one with Various Ketones: A Convenient Entry to 2-Methylene-1 -benzothiophen-3(2H)-one and/or 6H-Di[1]benzothieno[3,2-b:2,3-e]pyran Derivatives

1999 ◽  
Vol 23 (9) ◽  
pp. 542-543
Author(s):  
Alessandro Fraleoni ◽  
Paolo Zanirato
Keyword(s):  
Diethyl Ether ◽  
Boron Trifluoride ◽  
Room Temperature ◽  
Steric Factors ◽  
High Yields

The title compounds are obtained in moderate to high yields by BF3-assisted reaction of 1-benzothiophen-3(2 H)-one with nine ketones in diethyl ether at room temperature; the relative amounts of pyran 1 and ylidene 2 prove to be dependent upon electronic and steric factors.

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

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