938-10-3

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 4651, 1984 DOI: 10.1016/S0040-4039(01)91224-9

Upstream product

• 80-17-1 benzenesufonyl hydrazide 
• 7782-77-6 cis-nitrous acid 
• 54850-48-5 DL-alanyl chloride 
• 14860-69-6 (p-aminobenzene)sulfonyl azide 
• 141-78-6 ethyl acetate 
• 108-98-5 thiophenol 
• 970-88-7 2,4-dinitrophenyl benzenesulfonate 
• 368-43-4 phenylsulfonyl fluoride 
• 51-28-5 2,4-Dinitrophenol 
• 98-09-9 benzenesulfonyl chloride 
• 98-11-3 benzenesulfonic acid 
• 133745-75-2 N-fluorobis(benzenesulfon)imide 

Downstream Products

• 28460-28-8 N-(phenylsulfonylimino)pyridinium ylide 
• 624724-80-7 N-(naphthalen-1-yl)-1-phenylmethanesulfonamide 
• 98-10-2 benzenesulfonamide 
• 101731-54-8 benzenesulfonic acid-(2-anilino-anilide) 
• 83482-80-8 N¹-phenyl-N⁴-phenylsulfonyl-1,4-phenylenediamine 
• 6311-65-5 N-p-tolyl-benzenesulfonamide 
• 18457-86-8 N-o-tolyl-benzenesulfonamide 
• 1807-55-2 4,4'-methylenebis(N-methylaniline) 
• 1678-25-7 N-phenylbenzenesulfonamide 
• 123-30-8 4-amino-phenol 
• 95-55-6 2-amino-phenol 
• 591-27-5 m-Hydroxyaniline 
• 27806-96-8 N-<1,2,3-Trimethyl-buten-(2)-yliden>-benzolsulfonamid 
• 68018-68-8 C₁₂H₂₁N₂O₄PS 

Relevant academic research and scientific papers

One-pot synthesis of sulfonyl-1H-1,2,3-triazolyl-thiomorpholine 1,1-dioxide derivatives and evaluation of their biological activity

A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a–5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in?vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1-yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs.

Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature

A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.

Synthesis of Sulfonyl Azides via Lewis Base Activation of Sulfonyl Fluorides and Trimethylsilyl Azide

A protocol for the efficient conversion of sulfonyl fluorides into sulfonyl azides through Lewis base activation is described. The in situ generated sulfonyl azides are efficient diazo-transfer agents, affording diazo compounds and primary azides in excellent yields.

Nucleophilic Substitution Reactions of 2,4-Dinitrophenyl X-Substituted-Benzenesulfonates and Y-Substituted-Phenyl 4-Nitrobenzenesulfonates with Azide Ion: Regioselectivity and Reaction Mechanism

The second-order rate constants for reactions of 2,4-dinitrophenyl X-substituted-benzenesulfonates (4a-4f) and Y-substituted-phenyl-4-nitrobenzenesulfonates (5a-5f) with N3- ion have been measured spectrophotometrically. The reactions of 4a-4f proceed through S-O and C-O bond fission pathways competitively. Fraction of the S-O bond fission decreases rapidly as the substituent X in the benzenesulfonyl moiety changes from an electron-withdrawing group to an electron-donating group. The Hammett plots for reactions of 4a-4f are linear with ρX=1.87 and 0.56 for the S-O and C-O bond fission, respectively. The fact that the substituent X is further away from the reaction site of the C-O bond fission than that of the S-O bond fission is one reason for the smaller ρX value. The nature of the reaction mechanism (i.e., a stepwise mechanism in which expulsion of the leaving group occurs after the rate-determining step) is also responsible for the smaller ρX value obtained from the C-O bond fission. The Bronsted-type plot for the reactions of 5a-5f is linear with βlg=-0.63, which is typical for reactions reported previously to proceed through a concerted mechanism. Effects of substituents X and Y on regioselectivity and reaction mechanism are discussed in detail.

Direct synthesis of sulfonyl azides from sulfonic acids

A one-pot process for the synthesis of various sulfonyl azides (RSO2N3) by treating sulfonic acids with triphenylphosphine/trichloroisocyanuric acid/sodium azide at room temperature is described. A wide range of arenesulfonyl and alkanesulfonyl azides was obtained in excellent yields under mild conditions.

One-pot synthesis of sulfonamides and sulfonyl azides from thiols using chloramine-T

A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols was accomplished by oxidation with chloramine-T (=N-chlorotosylamide=N-chloro-4- methylbenzenesulfonamide), tetrabutylammonium chloride (Bu4NCl), and H2O. The sulfonyl chlorides were then further allowed to react with excess amine or NaN3 in the same pot.

Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N -chlorosuccinimide

A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water. The sulfonyl chlorides are then further allowed to react with excess amine or sodium azide in the same reaction vessel. Georg Thieme Verlag Stuttgart - New York.

POLYNUCLEOTIDE LABELING REAGENT

The present invention provides a new labeling reagent for preparing modified oligonucleotides and processes for their production wherein these oligonucleotides contain at least once the structure P═N—SO2-benzole-L-M-X, characterized in that L i

Convenient one-pot synthesis of sulfonyl azides from sulfonic acids

We have developed a one-pot process for preparing sulfonyl azides by treating sulfonic acids with trichloroacetonitrile, triphenylphosphine, and sodium azide at room temperature. A wide range of sulfonyl azides was synthesized in excellent yields under mild conditions. Georg Thieme Verlag Stuttgart.

Nucleophilic reactivity towards electrophilic fluorinating agents: Reaction with N-fluorobenzenesulfonimide ((PhSO2)2NF)

Second-order rate constants for the reaction of N-fluorobenzenesulfonimide (FBS) with nucleophilic reagents, kNu (M-1 s-1), have been measured in aqueous solution at 25°C. Analysis of the reaction products shows that soft polarizable nucleophiles (I-, SCN-, Br-) react at fluorine, whereas hard nucleophiles (oxygen and nitrogen nucleophiles) react at sulfur. The ambident behaviour of this electrophile seems to be related to the relative contribution of electrostatic and orbital interactions in reaching the transition state. The preferential reaction of soft nucleophiles at fluorine and the correlation of kNu values with the one-electron oxidation potentials of the nucleophiles in water suggest that nucleophilic reactivity at fluorine is largely determined by the ease of one-electron transfer from the nucleophile to the electrophile. Nucleophilic addition to fluorine is far more sensitive to the nature of the attacking nucleophile than the corresponding reactions at both saturated (n scale) and unsaturated carbon (N+ scale). Comparison of the rate constants for the reaction of nucleophiles at the sulfonyl group with those for reaction of the same nucleophiles with 2,4-dinitrophenyl acetate reveals a similar reactivity pattern for sulfonyl sulfur and carbonyl carbon as electrophilic centres.