Benzenesulphonyl deriv

A) Picrates (except diphenylamine). (B) Acetyl Derivatives. (C) Benzoyl, Toluene-p sulphonyl and Benzenesulphonyl Derivatives. (D)... 

It has been reported that the reaction of 2-(2-pyridyl)indole with benzene-sulphonyl chloride, under phase-transfer catalytic conditions, yields three products, which have been recorded as being the 3-, 4- and 6-benzenesulphonylindoles [56], or 3-chloro-l-benzenesulphonyl-2-(2-pyridyl)indole, as the major product, with the 1-benezenesulphonyl- and l,3-bis(benzenesulphonyl) derivatives, as the minor products [55]. In the light of the earlier discussion, the latter structural assignments appear to be more likely to be correct. 

The antihypertensive agent 278 has been 14C-labelled by carbonation of the 2-lithiated indole, 279 (R = Li), with 14CC>2 and subsequent combination with a preformed peptide side chain. In 279 (R = H) the indole nitrogen has been converted into its benzenesulphonyl derivative to direct properly the lithiation while the 2-hydroxy-3-isopropylaminopropoxy side chain has been protected as oxazolidin-2-one290. 

D. S. Brown, S. V. Ley, and S. Vile, Preparation of cyclic acetals from 2-benzenesulphonyl derivatives a new, mild glycosylation procedure, Tetrahedron Lett., 29 (1988) 4873-4876. 

Kataoka, H., Ohmi, S., Miyamoto, Y., and Makita, M., Determination of low molecular weight aliphatic primary amines in urine as their benzenesulphonyl derivatives by gas chromatography with flame photometric detection, Biomed. Chromatogr., 6, 251-254, 1992. 

Benzoyl and benzenesulphonyl derivatives have not been widely applied for chromatographic analyses, but because they can be detected in the ultraviolet they have found some use in HPLC. They are also used to make derivatives from volatile compounds as a means avoiding evaporative losses. They are readily made under Schotten-Baumann conditions. Thus, an amine solution (3 ml) is made alkaline with an equal volume of 7.5 M NaOH, and 50 fi of benzoyl choride is vigorously shaken with this solution until consumed. The product is extracted twice with 2 ml of diisopropyl ether, and the ether extracts are blown dry with nitrogen before being taken up in the ether for analysis [142]. A similar procedure was used for amines by Terashi et at. but using benzenesulphonyl chloride [143]. 

The amine is converted into the benzenesulphonyl derivative by means of bcnzenesulphonic chloride in the... 

The rates of displacement of the sulphonate group by azide ion in DMF at 110 °C have been measured for a series of toluene-p-sulphonyl and p-bromo-benzenesulphonyl derivatives of 3-0-methyl-cA/ra-inositol and 4-0-methyl-tf//< -inositol in these compounds, the arylsulphonate group was located at position 4 (or 3), and the substituents at positions 1,2, 5, and 6 were isopropylidene, acetyl, methyl, and cyclic carbonate. All of the resulting azides (except the unreactive penta-O-methyl-c/j/ra derivative) could be converted into one of two inosamine penta-acetates, viz. lL-2-amino-2-deoxy-l-0-methyl-a//o-inositol and 1d-3-amino-3-deoxy-4-0-methyl-c/ /ra-inositol penta-acetates. The results were discussed in terms of currently held views on displacement reactions with carbohydrate and related sulphonates. 

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