One-Pot Intermolecular C-S Self-Coupling of Dimethyl Sulfoxide Promoted by Molybdenum Pentachloride

2016 ◽  
Vol 2016 (23) ◽  
pp. 3838-3845 ◽  
Author(s):  
Marco Bortoluzzi ◽  
Eleonora Ferretti ◽  
Mohammad Hayatifar ◽  
Fabio Marchetti ◽  
Guido Pampaloni ◽  
...  
Keyword(s):  
Dimethyl Sulfoxide ◽  
One Pot ◽  
Molybdenum Pentachloride

Facile Approach to Geminal Heterodihalogenation. One-Pot Synthesis of α-Bromo-α-Chloro Ketones

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1430-1434
Author(s):  
Ming Bian ◽  
Jin-feng Zhou ◽  
Dong-min Tang
Keyword(s):  
Drug Discovery ◽  
Dimethyl Sulfoxide ◽  
Functional Groups ◽  
Methyl Ketones ◽  
One Pot ◽  
One Pot Synthesis ◽  
Operational Simplicity

An efficient and practical protocol for the geminal heterodihalogenation of methyl ketones by using readily available dimethyl sulfoxide and a combination of HCl and HBr is reported. Control experiments suggested that the acidity of the solution, as well as the oxidizing ability and nucleophilicity of the dimethyl sulfoxide might work cooperatively in ensuring the success of the tandem substitution. Its operational simplicity, easy accessibility, and mild oxidative conditions suggest that the present strategy might be useful for the assembly of bromochloromethyl functional groups in drug discovery.

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 Approach to Catalyst-Free Cyanation and Azidation of ­Organic Compounds and a One-Pot Preparation of 5-Substituted 1H-Tetrazoles by Using a Dimethyl Sulfoxide–Nitric Acid Combination

Synlett ◽  
2019 ◽  
Vol 30 (20) ◽  
pp. 2290-2294
Author(s):  
Mohammad Ali Nasseri ◽  
Seyyedeh Ameneh Alavi ◽  
Boshra Mahmoudi ◽  
Milad Kazemnejadi
Keyword(s):  
Nitric Acid ◽  
Dimethyl Sulfoxide ◽  
Organic Compounds ◽  
Sodium Azide ◽  
Potassium Cyanide ◽  
Hydroxylamine Hydrochloride ◽  
One Pot ◽  
Mild Conditions ◽  
Tetrazole Derivatives

In this study, cyanations or azidations of imines were performed by using hydroxy(dimethyl)-λ4-sulfanecarbonitrile or azido(dimethyl)-λ4-sulfanol, respectively, prepared in situ by treatment of potassium cyanide or sodium azide with a dimethyl sulfoxide–nitric acid combination. Furthermore, a one-pot preparation of 5-substituted 1H-tetrazole derivatives was carried out by using this reagent combination in the presence of an aldehyde, hydroxylamine hydrochloride, and sodium azide under mild conditions.

scholarly journals Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8–DMSO: application to the synthesis of vernakalant

2015 ◽  
Vol 11 ◽  
pp. 1008-1016 ◽  
Author(s):  
Dnyaneshwar N Garad ◽  
Subhash D Tanpure ◽  
Santosh B Mhaske
Keyword(s):  
Dimethyl Sulfoxide ◽  
Ammonium Persulfate ◽  
Primary Amines ◽  
Radical Mechanism ◽  
Forming Process ◽  
One Pot ◽  
Practical Synthesis ◽  
Cyclic Imides ◽  
Cyclic Anhydrides ◽  
High Yields

Ammonium persulfate–dimethyl sulfoxide (APS–DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.

ChemInform Abstract: Iodine-Mediated Copper-Catalyzed Efficient α-C(sp2)-Thiomethylation of α-Oxoketene Dithioacetals with Dimethyl Sulfoxide in One Pot.

ChemInform ◽  
2016 ◽  
Vol 47 (17) ◽  
Author(s):  
Gaurav Shukla ◽  
Abhijeet Srivastava ◽  
Anugula Nagaraju ◽  
Keshav Raghuvanshi ◽  
Maya Shankar Singh
Keyword(s):  
Dimethyl Sulfoxide ◽  
One Pot

ChemInform Abstract: A Convenient One-Pot Synthesis of Cystine-Containing Peptides from Protected Peptidyl Resins Using the Trimethylsilyl Chloride-Dimethyl Sulfoxide-Trifluoroacetic Acid System.

ChemInform ◽  
2010 ◽  
Vol 28 (12) ◽  
pp. no-no
Author(s):  
H. TAMAMURA ◽  
T. ISHIHARA ◽  
A. OTAKA ◽  
T. KOIDE ◽  
K. MIYOSHI ◽  
...  
Keyword(s):  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Acid ◽  
Acid System ◽  
One Pot ◽  
One Pot Synthesis
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