Synthesis and thermal decomposition of 1-methyl-1H,3H-1,2-benzisothiazole 1-oxide hydrochloride

Rynbrandt, Ronald H.; Balgoyen, Doris P.

doi:10.1021/jo00403a049

Cited by 18 publications

(6 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The major component was identified as benz [d ]isothiazole 26 (48%) by comparison of its NMR spectra with literature data. 12 Finally some 2-(phenylthio)benzyl alcohol 27 (≈6%) was obtained; this was subsequently discovered to be a very minor impurity in the starting material. The pyrolysate from the corresponding thiophenoxyl generator 18 also gave minor radical coupling products (biphenyl 24, diphenylmethane 28, and bibenzyl 29) but again benz [d ]isothiazole 26 (34%), identified as above, was found to be the major product.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals

Creed

Leardini

McNab

et al. 2001

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

“…13 C NMR spectrum 15 shows discrepancies at δ C 129 and 110); m/z 268 (M ϩ , 100%) and 134 (29). (12).…”

Section: Pyrolysis Experimentsmentioning

confidence: 99%

Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals

Creed

Leardini

McNab

et al. 2001

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

“…sulfuric acid is still one of the most important (Scheme 1, Path D). [73][74][75][76] Despite potential hazards associated with the application of hydrazoic acid, this method is of major importance for the large scale synthesis of the "key sulfoximine" rac-8 (Scheme 2 and Section 2.3). The major disadvantages of this entry are C-S-bond fission in the case of branched alkyl substituents and partial racemisation of non-racemic sulfoximines during the imination process.…”

Section: From Sulfoxides and Sulfiliminesmentioning

confidence: 99%

Sulfoximines: Structures, Properties and Synthetic Applications

2000

View full text Add to dashboard Cite

This review presents a comprehensive treatment of sulfoximine chemistry particularly emphasising synthetic developments and structural work after 1985. Following a brief introduction, the structures and properties of sulfoximines and metallated sulfoximines are discussed. The second section deals with the preparation of sulfoximines emphasising new methods. The main part of the review is concerned with reactions of sulfoximines. The material in this section is organised based on the reactivity pattern displayed by the various sulfoximines. Therefore they are grouped roughly into three classes of compounds. The first group of sulfoximines comprises compounds acting as C-nucleophiles, the second one contains electrophilic sulfoximines and the last group is made up of sulfoximines being useful as (chiral) ligands particularly for transition metals. Finally the ability of sulfoximines to act as "chiral chemical chameleons" and their rôle in biological and medicinal chemistry is briefly discussed.

show abstract

“…Three regioisomeric benzyl chloride derivatives were applied in the final step of the general synthesis outlined in Scheme . While 1-chloromethyl-2-methanesulfinyl-benzene and 1-chloromethyl-4-methanesulfinyl-benzene were synthesized according to literature procedures, 1-chloromethyl-3-methanesulfinyl-benzene 19 was prepared by the following route (Scheme ): LiAlH 4 reduction of 3-methylsulfanyl-benzoic acid yielded phenyl-methanol derivative 17 . Subsequent chlorination of 17 with SOCl 2 gave 1-chloromethyl-3-methylsulfanyl-benzene 18 which was readily oxidized with H 2 O 2 to yield sulfoxide 19 .…”

Section: Chemistrymentioning

confidence: 99%

From Imidazoles to Pyrimidines: New Inhibitors of Cytokine Release

Laufer

Wagner

2002

J. Med. Chem.

View full text Add to dashboard Cite

On the basis of model imidazole inhibitors of cytokine release, a series of novel pyridinyl pyrimidine derivatives was prepared and tested on their ability to inhibit the release of tumor necrosis factor-alpha (TNF-alpha) and interleukin-1beta (IL-1beta) from peripheral blood mononuclear cells (PBMC) and human whole blood. In the pyrimidine series, structure-activity relationships (SARs) similar to those of the imidazole series were found, although generally pyrimidine compounds were less potent. Modification of the substituent at the 2 position of the pyrimidine led to the most active compound 14 which inhibited release of TNF-alpha (IC(50) = 3.2 microM) and IL-1beta (IC(50) = 2.3 microM) from PBMC as effectively as the model imidazole inhibitor ML 3163 (TNF-alpha, IC(50) = 3.7 microM; IL-1beta, IC(50) = 0.9 microM). Screening in an isolated enzyme assay revealed both imidazole and pyrimidine compounds as inhibitors of p38 MAP (mitogen-activated protein) kinase.

show abstract

Synthesis and thermal decomposition of 1-methyl-1H,3H-1,2-benzisothiazole 1-oxide hydrochloride

Cited by 18 publications

References 5 publications

Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals

Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals

Sulfoximines: Structures, Properties and Synthetic Applications

From Imidazoles to Pyrimidines: New Inhibitors of Cytokine Release

Contact Info

Product

Resources

About