ChemInform Abstract: DABCO-Induced [2 + 2 + 2]-Cycloaddition Reaction of Ethyl Propiolate and Aryl Aldehydes for the Synthesis of 4-Aryl-4H-pyrans.

ChemInform ◽  
2010 ◽  
Vol 41 (18) ◽  
Author(s):  
Weibing Liu ◽  
Huanfeng Jiang ◽  
Peng Zhou ◽  
Shifa Zhu
Keyword(s):  
Cycloaddition Reaction ◽  
Aryl Aldehydes

DABCO-Induced [2+2+2]-Cycloaddition Reaction of Ethyl Propiolate and Aryl Aldehydes for the Synthesis of 4-Aryl-4H-pyrans

Synlett ◽  
2009 ◽  
Vol 2009 (20) ◽  
pp. 3295-3298
Author(s):  
Huanfeng Jiang ◽  
Weibing Liu ◽  
Peng Zhou ◽  
Shifa Zhu
Keyword(s):  
Cycloaddition Reaction ◽  
Aryl Aldehydes

Preparation of ortho-hydroxyalkylanilines as ortho-quinone methide imine precursors via an aminoborane complex

1995 ◽  
Vol 73 (9) ◽  
pp. 1506-1513 ◽  
Author(s):  
David Migneault ◽  
Michael A. Bernstein ◽  
Cheuk K. Lau
Keyword(s):  
Good Yield ◽  
Cycloaddition Reaction ◽  
Quinone Methide ◽  
Aliphatic Aldehydes ◽  
General Process ◽  
Aryl Aldehydes

A general process for ortho-specific hydroxyalkylation of secondary anilines has been developed. N-Methylanilinochlorophenylboranes react readily with aryl aldehydes, and with α,β-unsaturated or saturated aliphatic aldehydes to give the corresponding ortho-hydroxyalkylanilines in good yield. Thermolysis of the latter generated the corresponding ortho-quinone methide imine, which can participate in an electrocyclic or intramolecular [4 + 2] cycloaddition reaction to give various dihydro- and tetrahydroquinoline derivatives. Application of the method to the syntheses of 5-aza analogs of hexahydrocannabinol is demonstrated. Keywords: quinone methide imine, ortho-hydroxyalkylaniline, azacannabinoids.

Tuning the configuration of the flexible metal–alkene-framework affords pure cycloisomers in solid state photodimerization

2021 ◽  
Author(s):  
Yong Wang ◽  
Meng-Fan Wang ◽  
David James Young ◽  
Hua Zhu ◽  
Fei-Long Hu ◽  
...  
Keyword(s):  
Solid State ◽  
Cycloaddition Reaction ◽  
Guest Molecules ◽  
Flexible Metal

The bulkiness of the guest molecules influences the conformations of the ligand and the final outcomes of the cycloaddition reaction.

Nickel-Catalyzed Regioselective Hydroalkylation of 1,3-Dienes with Hydrazones

2019 ◽  
Author(s):  
Leiyang Lv ◽  
Dianhu Zhu ◽  
Zihang Qiu ◽  
Jianbin Li ◽  
Chao-Jun Li
Keyword(s):  
Catalytic Method ◽  
Unsaturated Hydrocarbons ◽  
Carbon Nucleophiles ◽  
Aryl Aldehydes ◽  
Aldehydes And Ketones ◽  
Sterically Hindered

Hydroalkylation of unsaturated hydrocarbons with unstablized carbon nucleophiles is difficult and remains a major challenge. The disclosed examples so far mainly focused on the involvement of heteroatom and/or stabilized carbon nucleophiles as efficient reaction partners. Reported here is an unprecedented regioselective nickel-catalyzed hydroalkylation of 1,3-dienes with hydrazones, generated in situ from abundant aryl aldehydes and ketones and acted as both the sources of unstabilized carbanions and hydride. With this strategy, both terminal and sterically hindered internal dienes are hydroalkylated efficiently in a highly selective manner, thus providing a novel and reliable catalytic method to construct challenging C(sp3)-C(sp3) bonds.

New Pyrrolo[1,2-b]pyridazine Derivatives by 1,3-Dipolar Cycloaddition of Mesoionic Oxazolopyridazinone

2008 ◽  
Vol 59 (11) ◽  
Author(s):  
Miron Teodor Caproiu ◽  
Florea Dumitrascu ◽  
Mino R. Caira
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridazine Derivatives ◽  
New Compounds

New pyrrolo[1,2-b]pyridazine derivatives 8a-f were synthesized by 1,3-dipolar cycloaddition reaction between mesoionic 1,3-oxazolo[3,2-b]pyridazinium-2-oxides and diethyl or diisopropyl acetylenedicarboxylate as alkyne dipolarophiles. The structures of the new compounds were assigned by elemental analysis and NMR spectroscopy.

Synthesis and Characterization of a Novel Ionic Liquid Based on N,N,N,N-tetramethylethylenediamine and its Application in the Synthesis of 1,8-dioxo-octahydro Xanthenes

2018 ◽  
Vol 21 (7) ◽  
pp. 526-532 ◽  
Author(s):  
Zahra Abdi Piralghar ◽  
Mohammad Mahmoodi Hashemi ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Chlorosulfonic Acid ◽  
Solvent Free ◽  
Aryl Aldehydes ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions ◽  
Aryl Aldehyde ◽  
High Yields

Aim and Objective: In this work, we synthesized and characterized a novel Brönsted acidic ionic liquid from the reaction of N, N, N’, N’-tetramethylethylenediamine with chlorosulfonic acid and explored its catalytic activity in 1, 8-dioxo-octahydroxanthenes synthesis. Materials and Methods: Dimedone, aryl aldehydes, and the ionic liquid as the catalyst were reacted under solvent-free conditions. The progressive of the reaction was monitored by a thin layer of chromatography (ethyl acetate/n-hexane = 1/5). All products were characterized as the basis of their spectra data and melting point by comparison with those reported in the literature. Results: The prepared ionic liquid was successfully applied in the synthesis of 1, 8-dioxooctahydroxanthenes in good to high yields on the reaction of aryl aldehyde and dimedone at 120oC under solvent-free conditions. Conclusion: This research demonstrates that the catalyst is impressive for 1, 8-dioxo-octahydroxanthenes synthesis under solvent-free conditions.

Synthesis of 2-(Substituted-silyl)thiophene-3-carboxylates via a Facile [3+2] Cycloaddition Reaction Catalyzed by Potassium tert-Butoxide

2016 ◽  
Vol 13 (7) ◽  
pp. 467-473 ◽  
Author(s):  
Yi-Nan Cheng ◽  
Wen-Bo Jin ◽  
Li-Min Wang ◽  
Shu-Jun Sun ◽  
Gui-Ying Xie ◽  
...  
Keyword(s):  
Cycloaddition Reaction
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