Hydrazides sulfonyl hydrazine

Acylhydrazines (s. a. Carboxylic acid hydrazides, Sulfonyl-hydrazines)... 

Lissamine rhodamine B sulfonyl hydrazine is a hydrazide derivative of sulforhodamine B that can spontaneously react with aldehyde- or ketone-containing molecules to form a covalent,... 

Texas Red hydrazide is a derivative of Texas Red sulfonyl chloride made by reaction with hydrazine (Invitrogen). The result is a sulfonyl hydrazine group on the No. 5 carbon position of the lower-ring structure of sulforhodamine 101. The intense Texas Red fluorophore has a QY that is inherently higher than either the tetramethylrhodamine or Lissamine rhodamine B derivatives of the basic rhodamine molecule. Texas Red s luminescence is shifted maximally into the red region of the spectrum, and its emission peak only minimally overlaps with that of fluorescein. This makes derivatives of this fluorescent probe among the best choices of labels for use in double-staining techniques. 

Lissamine rhodamine B sulfonyl hydrazine is a hydrazide derivative of sulforhodamine B that can spontaneously react with aldehyde- or ketone-containing molecules to form a covalent, hydrazone linkage (Fig. 217). It also can be used to label cytosine residues in DNA or RNA by use of the bisulfite activation procedure (Chapter 17, Section 2.1). The resulting fluorescent derivative exhibits an excitation maximum at a wavelength of 556 nm and a maximal emission wavelength of 580 nm when dissolved in methanol. In... 

The hydrazide derivative can be used to modify aldehyde- or ketone-containing molecules, including cytosine residues using the bisulfite activation procedure described in Chapter 17, Section 2.1. The sulfonyl hydrazine group of Texas Red hydrazide reacts with aldehydes or ketones in target functional groups to form hy-drazone bonds (Fig. 218). Carbohydrates and glycoconjugates can be specifically labeled at the polysaccharide portion if the required aldehydes are first formed by periodate oxidation or another such method (Chapter 1, Section 4.4). 

SYNS BENZENESULFOHYDRAZIDE BENZENESULFONIC ACID, HYDRAZIDE BENZENE-SULFONOHYDRAZIDE BENZENE-SULFONYL HYDRAZIDE BENZENESULFONYL HYDRAZINE BENZENE SULPHONOHYDRAZIDE CELOGEN BSH... 

BSH Phenyl sulfohydrazide Phenyl sulfonyl hydrazide Phenyl sulfonyl hydrazine... 

Phenyl sulfone. See Diphenyl sulfone Phenylsulfonic acid. See Benzenesulfonic acid Phenyl sulfonyl hydrazide Phenyl sulfonyl hydrazine. See Benzenesulfonyl hydrazide N-(4-Phenylsulfonyl-o-tolyl)-1,1,1-trifluoromethanesulfonamide. See Perfluidone Phenyl-(3-sulfopropyl) ether, potassium salt CAS 89574-82-3 Empirical C9H11KO4S Uses Intermediate for dyes Trade Name Synonyms PSP [Raschig AG http //www. raschig. de]... 

Synonyms Benzenesulfohydrazide Benzenesulfonic acid, hydrazide Benzenesulfonic hydrazide Benzenesulfonohydrazide Benzenesulfonyl hydrazine BSH Phenyl sulfohydrazide Phenyl sulfonyl hydrazide Phenyl sulfonyl hydrazine... 

The conversion of esters to hydrazides and of hydrazides to the sulfonyl derivatives occurs in good yield in the McFadyen-Stevens synthesis, but the decomposition of sulfonyl derivatives gives low yields of the desired products, for example, thiazole hydrazide (28) with 10% excess of PhSOjCl in pyridine gave a 75% yield of l-phenylsulfonyl-2-(4-methyl-5-thiazo ecarbonyl)hydrazine (29) (66). The Newman-Caflish modification of the McFadyen-Stevens synthesis gave 37% 4-methyl-5-thiazole-carboxaldehyde (30) (Scheme 27). 

All the sulfonic acid hydrazides are made from hydrazine or semicarbazide and the appropriate sulfonyl chloride in the presence of an HCl acceptor such as ammonia. 

The carbon-carbon double bond can be reduced by diimide prepared in solution in a number of ways.34 183,184 Oxidation of hydrazine with oxygen (air) or H202 in the presence of a catalytic amount of Cu(II) ion was the first method to generate and use diimide in hydrogenation.183-185 Acid-catalyzed decomposition of alkali azido-dicarboxylates,185,186 as well as thermal or base-catalyzed decomposition of aromatic sulfonyl hydrazides,183,184 are also useful methods for preparing the diimide reducing agent. 

Most 1-aminopyrroles have been synthesised from y-diketones and a substituted hydrazine. If the parent N- aminopyrrole is desired, a hydrolyzable hydrazine derivative is used, for example semicarbazide or an acyl- or sulfonyl-hydrazide (equation 182) (B-77MI30607). 

Diimide occurs only as an unstable intermediate in the hydrolysis of azodi-carboxylic acid, in the alkaline cleavage of benzene sulfonyl hydrazide, hydroxyl-amine-O-sulfonic acid and chloramine, in the oxidation of hydrazine, and in several other organic decomposition reactions . At room temperature it readily undergoes decomposition, disproportionation, and in the presence of symmetrical multiple bonds (like the ones in olefins) hydrogen transfer reactions ... 

Sulfonyl chlorides (51) are important intermediates in the synthesis of a range of sulfonyl derivatives since the chlorine atom is readily replaced by nucleophilic reagents such as amines, alcohols and hydrazine to give the corresponding sulfonamides (57), sulfonates (58) and hydrazides (59) (Scheme 35). 

These derivatives (59) are generally obtained by condensation of the appropriate sulfonyl chloride (51) with an excess of hydrazine (Scheme 53). Sulfonyl hydrazides (59) react with nitrous acid (sodium nitrite-dilute acid) to form the corresponding sulfonyl azides (84), and with carbonyl compounds they yield the sulfonyl hydrazones (85) (Scheme 54). 

Functional group substituents on N-l of 2-pyrazolin-5-ones (Table XXXVII) are acyl, sulfonyl and various carboxyl derivatives, such as carbalkoxy, amides, thioamides, hydrazides, thiohydrazides and amidines. The usual synthesis of these compounds is by the classical 2-pyrazolin-5-one synthesis, reaction of a /J-ketoester with a hydrazine. In these cases the hydrazines are special types such as hydrazide,... 

Synonyms Benzenesulfonic acid, oxybis-, dihydrazide Diphenyloxide-4,4 -disulfohydrazide OBSH p,p -Oxybisbenzene disulfonylhydrazide 4,4 -Oxybis (benzenesulfohydrazide) Oxybisbenzenesulfonic acid dihydrazide Oxybis (benzenesulfonyl hydrazide) p,p -Oxybis benzene sulfonyl hydrazide, 4,4 -Oxybis (benzenesulfonyl) hydrazine p,p -Oxybis (benzylsulfonyl) hydrazide 4,4 -Oxydibenzenesulfonyl hydrazide Empirical C12H14N4O5S2 Formula H2NNHSO2C7H4OC6H4SO2NHNH2 Properties Wh. fine cryst. powd., odorless sol. in acetone moderately sol. in ethanol, polyethylene glycol insol. in gasoline and water m.w. 358.40 dens. 1.52 m.p. 150 C (dec.) gas yield 120-125 cc/g... 

The corresponding sulfonylamino acid methyl esters 518 were prepared by treatment of the sulfonylamino acids 517 with absolute methanol-pure thionyl chloride at low temperature (—5 °C to —10 °C). The esters 518, by hydrazinolysis with hydrazine hydrate, afforded the hydrazides 519. The sulfonylamino acids 517 were coupled with the appropriate amino acid methyl ester hydrochloride in THF-water-triethylamine mixture using DCC as the coupling reagent to yield the corresponding sulfonylamino dipeptide methyl esters 520 (Scheme 16). The synthetic sequence depicted in Scheme 16 has been successfully applied to a number of different aromatic sulfonyl chlorides as illustrated by the following examples. 

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