Sulfamides

Figure 2-31. Sample SOfile for sulfamide (sulfuric diamide).

Amides. Names for amides are derived from the names of the acid radicals (or from the names of acids by replacing acid by amide) for example, S02(NH2)2, sulfonyl diamide (or sulfuric diamide) NH2SO3H, sulfamidic acid (or amidosulfuric acid). 

Iodine reacts with sulfuryl chloride ia the presence of aluminum chloride as catalyst-forming iodine chlorides. Sulfuryl chloride reacts with anhydrous ammonia yielding a series of sulfamides of the general formula NH2S02(NHS02) NH2, where n > 0. A cycHc compound of the formula... 

Figure 15.50 The structures of (a) sulfamic acid, (b) the sulfamate ion, and (c) sulfamide.

In the solid state sulfamic acid forms a strongly H-bonded network which is best described in terms of zwitterion units +H3NSO3" rather than the more obvious formulation as aminosulfuric acid, H2NS02(0H). The zwitterion has the staggered configuration shown in Fig. 15.50a and the S-N distance is notably longer than in the sulfamate ion or sulfamide. 

Sulfamide, (H2N)2S02, can be made by ammonolysis of SO3 or O2SCI2. It is a colourless crystalline material, mp 93°, which begins to decompose above this temperature. It is soluble in water to give a neutral non-electrolytic solution but in boiling water it decomposes to ammonia and sulfuric acid. The structure (Fig. 15.50c)... 

This class of aziridine-forming reaction includes the first reaction reported to afford aziridines. In 1888 Gabriel reported that aziridines could be prepared in a two-step process, by chlorination of ethanolamines with thionyl chloride, followed by alkali-induced cyclization [75]. Wenker subsequently reported that heating of 600 g of ethanolamine with more than 1 kg of 96 % sulfuric acid at high temperature produced P-aminoethyl sulphuric acid 282 g of it was distilled from aqueous base to give 23 g of aziridine itself, the first preparation of the parent compound in a pure condition [76]. Though there is no evidence to substantiate the hypothesis, the intermediate in these reactions is perhaps a cyclic sulfamidate (Scheme 4.51). 

The amide 33l06b and the cyclic sulfamide 34106c, both C2-symmetric, and the borneol derived amide 3510bd provide further ways to xyn-aldols with remarkable induced diastereoselectivity. 

Ref 10) and by fluorination of 1) cyanuric acid (Ref 5) 2) sulfamide, yield 45% (Ref 14) [Kelly and Sukornick found that sulfamic acid, w, and F will react continuously in a flow re-... 

Other types of HIV-1 protease inhibitors have also been prepared using microwave-promoted Suzuki reaction [37]. The symmetric cyclic sulfamide (3K,4S,5S,6it)-3,6-bis(phenoxymethyl)-2,7-bis[4-(2-thienyl)benzyl]-l,2,7-thi-adiazepane-4,5-diol 1,1-dioxide, for instance, was synthesized via cross-couphng of (3aS,4R,8it,8aS) - 5,7 - bis(4 - bromobenzyl) - 2,2 - dimethyl - 4,8 - bis-(phenoxymethyl) hexahydro [1,3] dioxolo [4,5 - d] [ 1,2,7 ] - thiadiazepine 6,6 - dioxide with 2-thienylboronic acid for 3 min at 45 W (Scheme 19). 

For the addition of an organometailic compound to an imine to give a primary amine, R in RCH=NR would have to be H, and such compounds are seldom stable. However, the conversion has been done, for R = aryl, by the use of the masked reagents (ArCH=N)2S02 [prepared from an aldehyde RCHO and sulfamide (NH2)2S02]. Addition of R"MgX or R"Li to these compounds gives ArCHR"NH2 after hydrolysis. ... 

Desamin Same (Savoma) Imidazyl (Recordati) Imizol (Farmigea) Naftazolina (Bruschettini) Pupilla (Alfa Wassermann) Rinazina (Maggioni) Rinazina Senza Sulfamide (Maggioni)... 

Dichloro-2-N-octyl-isothiazolin-3-one and 2-methylthio-4-tert-butylamino-6-cyclopropylamino-S-triazine or N,N-dimethyl-N -phenyl-N -fluorodichloromethylthio)sulfamide Anthraquinones Free halogen sources with 5,5-dimethylhydantoin,... 

Finally, Katsuki and coworkers [271] described an enantioselective Ru-catalyzed domino reaction, which includes a sulfamidation of an aryl allyl sulfide 6/3-111 using the chiral Ru(salen)-complex 6/3-115, followed by a 2,3-sigmatropic rearrangement of the formed 6/3-112 to give N-allyl-N-arylthiotoluenesulfonamides 6/3-113. On hydrolysis, 6/3-113 yielded N-allyltoluenesulfonamides 6/3-114 (Scheme 6/3.33). The enantioselectivity ranged from 78 to 83% ee. 

Reactions of ester derivatives 243 with sulfamidate 244 gave the corresponding pyrazinones 245 in excellent yields (Equation 31) <2006BML1207>. 

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