Eco-friendly and regioselective synthesis of 3-(isoxazol-5)-yl) indoles from β-ethylthio-β-indolyl-α, β-unsaturated ketones in water

2021 ◽  
pp. 1-7
Author(s):  
Jia Jia ◽  
Ye Su ◽  
Hai-Feng Yu ◽  
Hai-Tao Du ◽  
Ze-Min Mei
Keyword(s):  
Regioselective Synthesis ◽  
Unsaturated Ketones

One-pot Synthesis of α,β-Unsaturated Ketones through Sequential Alkyne Dimerization/Hydration Reactions using Hoveyda-Grubbs Catalyst

2021 ◽  
Author(s):  
Bengi Öztürk ◽  
Begüm Sarıaslan ◽  
Mina Aşkun ◽  
Zeynep Tunalı ◽  
Solmaz Karabulut
Keyword(s):  
Regioselective Synthesis ◽  
Grubbs Catalyst ◽  
One Pot ◽  
Unsaturated Ketones ◽  
One Pot Synthesis

Herein we report a sequential one-pot alkyne dimerization/hydration protocol for the regioselective synthesis of α,β-unsaturated ketones in quantitive yields. The alkyne dimerization reactions of terminal arylacetylenes proceeded with high regioselectivity...

Regioselective Synthesis of Isomeric 3-[1-Substituted Pyrazol-3(5)-yl]indoles from β-Ethylthio-β-indolyl-α,β-unsaturated Ketones

Synthesis ◽  
2020 ◽  
Vol 52 (14) ◽  
pp. 2111-2120
Author(s):  
Zemin Mei ◽  
Haifeng Yu ◽  
Peiqiu Liao
Keyword(s):  
Regioselective Synthesis ◽  
Unsaturated Ketones ◽  
Cyclocondensation Reaction

An efficient and highly regioselective synthesis of isomeric 3-[1-substituted pyrazol-3(5)-yl]indoles has been developed by the acid-mediated regioselective cyclocondensation reaction of β-ethyltho-β-indolyl-α,β-unsaturated ketones and monosubstituted hydrazines. In the presence of 1 equivalent of AcOH in refluxing EtOH, the cyclocondensation reaction of β-ethyltho-β- indolyl-α,β-unsaturated ketones with monosubstituted hydrazines yielded 3-(1-substituted pyrazol-5-yl)indoles in excellent yields, while 3-(1-substituted pyrazol-3-yl)indoles were obtained in good yields when the cyclocondensation reaction was carried out in refluxing AcOH.

ChemInform Abstract: Intermolecular Rhodium-Catalyzed Hydroacylation of Allenes: The Regioselective Synthesis of β,γ-Unsaturated Ketones.

ChemInform ◽  
2009 ◽  
Vol 40 (44) ◽  
Author(s):  
Helen E. Randell-Sly ◽  
James D. Osborne ◽  
Robert L. Woodward ◽  
Gordon S. Currie ◽  
Michael C. Willis
Keyword(s):  
Regioselective Synthesis ◽  
Unsaturated Ketones

Complementary and Regioselective Synthesis of Isomeric 3-[Isoxazol-3(or 5)-yl]indoles from β-Ethylthio-β-indolyl-α,β-unsaturated Ketones

Synthesis ◽  
2021 ◽  
Author(s):  
Haifeng Yu ◽  
Wenju Wang ◽  
Kehua Wang ◽  
Xue Zhang
Keyword(s):  
Efficient Method ◽  
Hydroxylamine Hydrochloride ◽  
Regioselective Synthesis ◽  
Unsaturated Ketones ◽  
Cyclocondensation Reaction

AbstractA simple and efficient method for the complementary and regioselective synthesis of isomeric 3-(isoxazol-5-yl)indoles and 3-(isoxazol-3-yl)indoles has been developed by the regioselective cyclocondensation reaction of β-ethylthio-β-indolyl-α,β-unsaturated ketones and hydroxylamine hydrochloride. It was found that the cyclocondensation reaction in the presence of excess NaOEt in refluxing EtOH gives 3-(isoxazol-5-yl)indoles in good yields, whereas using NaOAc in boiling AcOH gives 3-(isoxazol-3-yl)indoles in good yields.

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