scholarly journals Efficient Synthesis of Isoquinoline Derivatives through Sequential Cyclization–Deoxygenation Reaction of 2-Alkynylbenzaldoximes

SynOpen ◽  
2022 ◽  
Vol 06 (01) ◽  
pp. 11-15
Author(s):  
Saeed Balalaie ◽  
Mojtaba Ayoubi ◽  
Ali Nikbakht ◽  
Kamran Amiri ◽  
Alireza Abbasi Kejani ◽  
...  
Keyword(s):  
Efficient Synthesis ◽  
Cyclization Reactions ◽  
Cyclic Nitrones ◽  
Silver Triflate ◽  
High Yields ◽  
Isoquinoline Derivatives

AbstractWe describe a novel, simple, robust, and efficient cyclization/deoxygenation approach for the synthesis of functionalized isoquinoline derivatives. Over the course of continued studies on o-alkynylbenzaldoxime cyclization reactions, the formation of cyclic nitrones through 6-endo-dig cyclization was achieved using silver triflate or bromine as an electrophile, and subsequently, the deoxygenation process was carried out in the presence of CS2 in good to high yields.

Efficient Synthesis of O-tert-Propargylic Oximes via Nicholas Reaction

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3461-3465
Author(s):  
Itaru Nakamura ◽  
Keigo Shiga ◽  
Mao Suzuki ◽  
Masahiro Terada
Keyword(s):  
Ammonium Nitrate ◽  
Efficient Synthesis ◽  
Propargylic Alcohols ◽  
Cyclic Nitrones ◽  
Acidic Catalysts ◽  
Nicholas Reaction ◽  
High Yields ◽  
Dicobalt Hexacarbonyl ◽  
Cerium Iv Ammonium Nitrate

A synthetic protocol to access O-tert-propargylic oximes derived from tertiary propargylic alcohols was established via Nicholas reaction. Thus, BF3·OEt2-mediated reaction between the dicobalt hexacarbonyl complex of tert-propargylic alcohols and p-nitrobenzaldoxime followed by decomplexation with cerium(IV) ammonium nitrate afforded the corresponding O-tert-propargylic oximes in good to high yields. The obtained O-tert-propargylic oximes were effectively converted into heterocycles, such as four-membered cyclic nitrones, oxazepines, and isoxazolines, by using π-Lewis acidic catalysts.

An Efficient Synthesis of 2-Substituted Quinazolin-4(3H)-ones by Using Recyclable Wang Resin Supported Sulfonic Acid Catalyst

2020 ◽  
Vol 17 ◽  
Author(s):  
Kalyani K. ◽  
Srinivasa Reddy Kallam
Keyword(s):  
Sulfonic Acid ◽  
Functional Group ◽  
Acid Catalyst ◽  
Sulphonic Acid ◽  
Isatoic Anhydride ◽  
Efficient Synthesis ◽  
Wang Resin ◽  
Polymer Supported ◽  
High Yields

Abstract:: An efficient synthesis of 2-substituted Quinazolin-4(3H)-ones has been developed from isatoic anhydride with various amidoximes by using recyclable polymer supported sulphonic acid catalyst. Excellent functional group compatibil-ity and high yields are the important features of this protocol.

scholarly journals PEG-embedded KBr3: A recyclable catalyst for multicomponent coupling reaction for the efficient synthesis of functionalized piperidines

2011 ◽  
Vol 7 ◽  
pp. 1334-1341 ◽  
Author(s):  
Sanny Verma ◽  
Suman L Jain ◽  
Bir Sain
Keyword(s):  
Coupling Reaction ◽  
Recyclable Catalyst ◽  
Efficient Synthesis ◽  
Molecular Bromine ◽  
Keto Ester ◽  
One Step ◽  
High Yields ◽  
Multicomponent Coupling ◽  
Three Component Coupling

PEG-embedded potassium tribromide ([K+PEG]Br3 −) was found to be an efficient and recyclable catalyst for the synthesis of functionalized piperidines in high yields in a one step, three component coupling between aldehyde, amine and β-keto ester. At the end of the reaction the [K+PEG]Br3 − was readily regenerated from the reaction mixture by treating the residue containing [K+PEG]Br− with molecular bromine.

Three-Component Synthesis of 4-Arylidene-3-alkylisoxazol-5(4H)-ones in the presence of potassium 2,5-dioxoimidazolidin-1-ide

2021 ◽  
Vol 25 ◽  
Author(s):  
Neda Reihani ◽  
Hamzeh Kiyani
Keyword(s):  
Ethylene Glycol ◽  
Ethyl Acetoacetate ◽  
Reaction Medium ◽  
Hydroxylamine Hydrochloride ◽  
Aromatic Aldehydes ◽  
Catalyst Loading ◽  
Efficient Synthesis ◽  
Current Process ◽  
High Yields ◽  
Low Catalyst Loading

: An efficient synthesis of 4-arylidene-3-alkylisoxazole-5(4H)-ones has been implemented via the three-component cyclocondensation of aryl(heteroaryl)aldehydes with hydroxylamine hydrochloride and β-ketoesters. The potassium 2,5-dioxoimidazolidin-1-ide has been introduced as the new organocatalyst to facilitate of this heterocyclization. In the current process, three starting materials, including substituted benzaldehydes/heterocyclic aromatic aldehydes, hydroxylamine hydrochloride, and ethyl acetoacetate/propyl acetoacetate/butyryl acetoacetate have been successfully used for the synthesize of the number of substituted isoxazole-5(4H)-ones in good to high yields in ethylene glycol as a green reaction medium at 80 ºC. The low catalyst loading is also a main advantage over the some reported catalysts.

scholarly journals A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 3031 ◽  
Author(s):  
Xiaodong Tang ◽  
Songlei Zhu ◽  
Ying Ma ◽  
Ren Wen ◽  
Lanqi Cen ◽  
...  
Keyword(s):  
Environmentally Benign ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Dicarbonyl Compounds ◽  
Pyrrole Derivatives ◽  
Three Component Reaction ◽  
High Yields ◽  
Operational Simplicity

A green, convenient and tandem procedure for the efficient synthesis of highly substituted indeno[1,2-b]pyrrole and acenaphtho[1,2-b]pyrrole derivatives by domino three-component reaction of tryptamine/benzylamine, 1,3-dicarbonyl compounds and ninhydrin/ acenaphthenequinone is described. The significant features of this procedure were characterized by mild reaction conditions, high yields, operational simplicity and it being environmentally benign.

scholarly journals Complex chromene derivatives through a silver-catalysed cascade reaction of simple o-alkynylsalicylaldehydes and alkenes

2016 ◽  
Vol 52 (91) ◽  
pp. 13405-13408 ◽  
Author(s):  
Tamara Arto ◽  
Patricia Fernández ◽  
Francisco J. Fañanás ◽  
Félix Rodríguez
Keyword(s):  
Cascade Reaction ◽  
Cyclization Reactions ◽  
Silver Triflate ◽  
Complex Transformation

Silver triflate catalyses a complex transformation of simple ortho-alkynylsalicylaldehydes and alkenes to give benzo[de]chromenyl ketones in a process that involves two formal [4+2]-cyclization reactions.

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.

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