17688-68-5

Usage

Uses

Used in Cardiovascular Applications:
4-Phenylthiomorpholine 1,1-dioxide is used as an antihypertensive and heart failure medication for the treatment of high blood pressure and heart failure. It operates by relaxing blood vessels and slowing the heart rate, thereby improving blood flow and reducing blood pressure.
Used in Post-Heart Attack Recovery:
In the healthcare industry, 4-Phenylthiomorpholine 1,1-dioxide is utilized as a preventive measure to avoid further heart damage after a heart attack, contributing to the recovery process and the maintenance of cardiac health.

InChI:InChI=1/3C2H4O2.Ce.H2O/c3*1-2(3)4;;/h3*1H3,(H,3,4);;1H2/q;;;+3;/p-3

Upstream product

• 77-77-0 Divinyl sulfone 
• 62-53-3 aniline 
• 77-79-2 3-Sulfolene 
• 39093-93-1 thiomorpholine 1,1-dioxide 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 98-95-3 nitrobenzene 
• 471-03-4 bis(2-chloroethyl)sulfone 
• 358-79-2 bis-(2-fluoro-ethyl)-sulfone 

Downstream Products

• 39093-93-1 thiomorpholine 1,1-dioxide 
• 27913-96-8 4-(1,1-dioxo-4-thiomorpholin-4-yl)benzaldehyde 
• 55330-78-4 4-phenyl-1-thia-4-azacyclohexane 
• 102101-86-0 4-[4-(1,1-Dioxo-1λ⁶-thiomorpholin-4-yl)-phenylazo]-benzonitrile 
• 102101-87-1 [4-(1,1-Dioxo-1λ⁶-thiomorpholin-4-yl)-phenyl]-(4-nitro-phenyl)-diazene 
• 78866-05-4 [4-(1,1-Dioxo-1λ⁶-thiomorpholin-4-yl)-phenyl]-(4-methoxy-phenyl)-diazene 
• 102101-84-8 (4-Chloro-phenyl)-[4-(1,1-dioxo-1λ⁶-thiomorpholin-4-yl)-phenyl]-diazene 
• 102101-85-9 [4-(1,1-Dioxo-1λ⁶-thiomorpholin-4-yl)-phenyl]-(4-trifluoromethyl-phenyl)-diazene 

Relevant academic research and scientific papers

Catalyzed double Michael addition of anilines to vinyl sulfone

Substituted anilines and vinyl sulfone undergo a facile double Michael addition to form substituted phenylthiomorpholine dioxide, catalyzed with AlCl3 or H3PO4. Scope and conditions were explored.

Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity

We report an investigation of the Chan-Lam amination reaction. A combination of spectroscopy, computational modeling, and crystallography has identified the structures of key intermediates and allowed a complete mechanistic description to be presented, including off-cycle inhibitory processes, the source of amine and organoboron reactivity issues, and the origin of competing oxidation/protodeboronation side reactions. Identification of key mechanistic events has allowed the development of a simple solution to these issues: manipulating Cu(I) → Cu(II) oxidation and exploiting three synergistic roles of boric acid has allowed the development of a general catalytic Chan-Lam amination, overcoming long-standing and unsolved amine and organoboron limitations of this valuable transformation.

Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem

The Chan-Evans-Lam reaction is a valuable C-N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan-Evans-Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found to enable effective C-N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines.

Boric acid/glycerol as an efficient catalyst for synthesis of thiomorpholine 1,1-dioxide by double michael addition reaction in water

Thiomorpholine 1,1-dioxides were prepared with double Michael addition reaction of aromatic amines to divinyl sulfone catalyzed by boric acid/glycerol in water. This catalyst system was also used for the Michael addition reaction of aromatic amines to electron-deficient alkenes. The reaction is simple and green and gives good to excellent yields.

One-pot aryl-1,4-thiomorpholine 1,1-dioxide synthesis via double 1,4-addition of in situ reduced nitroarenes to divinyl sulfones

One-pot reduction-triggered double aza-Michael type 1,4-addition reactions of various nitroarenes to divinyl sulfones were investigated. In the presence of indium/AcOH in MeOH or in sat. aq NH4Cl/MeOH, nitroarenes and divinyl sulfones were cycl

Synthesis of Piperazines and Thiomorpholines by Ozonolysis of Cyclic Olefins and Reductive N-Alkylation

Ozonized 1-trifluoroacetyl-3-pyrroline (2a) and 3-sulfolene (6) were reduced with sodium cyanoborohydride (1) to afford the dialdehyde, which reacted in situ with the primary amines 3ad in the presence of 1 to give the piperazines 4ad (2160 percent) and the dioxothiomorpholines 7ad (2676 percent).Reduction of 7a and 7c with diisobutylaluminum hydride yielded the thiomorpholines 8a and 8c, respectively.On the other hand, the 9-membered azacrown ethers 10 and 11 were obtained when N,N'-dibenzylethylenediamine (9) was employed.The dioxothiomorpholine derivatives 13 of amino acids were also prepared by the same treatment.

THE EFFECTS OF CYCLIC TERMINAL GROUPS IN 4-AMINOAZOBENZENE AND RELATED AZO DYES. PART 3. ELECTRONIC ABSORPTION SPECTRA OF SOME MONOAZO DYES DERIVED FROM N-PHENYLMORPHOLINE, N-(PHENYL)THIOMORPHOLINE, N-(PHENYL)THIOMORPHOLINE 1,2-DIOXIDE, AND N-ACETYL-N'-PHENYLPIPERAZINE

Monoazo dyes containing a terminal morpholino group absorp hypsochromically in comparison with their piperidino counterparts as a result of electron withdrawal by the oxygen atom.Similar shifts are observed with related dyes possessing other γ-heteroatoms in the donor group.In acid solution, protonation takes place at the β-azo nitrogen atom (azonium tautomer) and at the terminal nitrogen atom (ammonium tautomer) to an extent which depends on the inductive effect of the γ-substituent.