Sulfonamide aniline

SYNS ALBEXAN ALBOSAL AMBESIDE p-.UIINOBENZENESULFAMIDE p-AMINO-BENZENESULFONAMIDE 4-AMINOBENZENE-SULFONAMIDE p-AMINOPHENYLSULFONAMIDE 4-AMINOPHENYLSULFONAMIDE p-ANILINE-SULFONAMIDE ANILINE-p-SULFONIC AMIDE ANTISTREPT BACTERAMID COLLOMIDE COLSULANYDE COPTICIDE DIPRON ESTREPTOCEDA F 1162 FOURNEAU 1162 GERISON GOMBARDOL LUSIL LYSOCOCCINE... 

Keywords large scale, phthalic anhydride, aniline sulfonamide, phthalazole, solid-solid reaction, solid-solid reaction, ball mill... 

The development of catalytic methods for the hydroamination of nonactivated alkenes, allenes, and alkynes has received considerable attention in recent years [1]. These highly atom-economical processes allow direct access to industrially and biologically relevant classes of compounds such as amines, enamines, and imines from cheap and readily available starting materials. This has recently led to an ever-increasing range of molecular compounds that have been identified as catalysts for these transformations (Scheme 13.1). Whereas rare-earth catalysts have been found to be mainly active in intramolecular hydroamination, other catalysts - in particular those of the late transition metals - are frequently limited to the addition of weakly basic substrates (aniline, sulfonamides, carboxamides, etc.) to alkenes, alkynes, and allenes. 

AMNES - AMINES, AROMATIC - ANILINE AND ITS DERIVATIVES] (Vol 2) [ANTIBACTERIALAGENTSSYNTHETIC - SULFONAMIDES] (Vol2)... 

Several reactions take place during heating of 2-nitrobenzenesulphenanilides 355 without solvent or in excess of the corresponding aniline at 195 °C. Originally 4-amino derivative 357 was reported to be the main product (35JA1517). However, later reinvestigation found sulfonamide 356 as the principle product. It was also... 

The group of Caddick has described the synthesis of functionalized sulfonamides by microwave-assisted displacement of pentafluorophenyl (PFP) sulfonate esters with amines (Scheme 6.159) [306]. Their ease of handling due to their higher crystallinity, along with their long shelf-life and their ability to react under aqueous reaction conditions, makes these an attractive alternative to sulfonyl chlorides. The microwave-assisted reaction of alkyl PFP esters with amines is a facile process which proceeds cleanly and in good yields with a number of different amines, including primary, secondary, and sterically hindered amines, and anilines. Optimum condi-... 

For a general, simple high yield indole synthesis from anilines and methylthioacetaldehyde etc. see JACS 95,588,591,2718,6508 (1973). For indoles from N-( /3 -hydroxy-ethyl aniline esters see BSC 2485(1973). For a 2-acyl-indoles in one step from orthoamino-ketones and alpha-haloketones or 2-carboxyindoles from sulfonamides of ortho-aminocarbonyls see JOC 38,3622-24(1972). Indole and 5-Br-indole in 4 steps from beta-naphthol see Chem. Het. Cpds. (Russ.) 753(1973). Indole-JOC 37,3622(1972). 

In the presence of tetramethyltin, 1-bromonauclefine reacts with CO in a Pd-catalyzed carbonylation to give the alkaloid naucletine [202], Dong and Busacca effected a new synthesis of tryptamines and tryptophols via a Rh-catalyzed hydroformylation of functionalized anilines that are prepared by a standard Heck reaction, as shown for the preparation of tryptamine sulfonamide 325 [423]. This reaction is applicable to ring-substituted tryptamines (Cl, Br, F. OMe, CF3). Likewise, the Rh-catalyzed carbonylation of o-alkynylanilines, which were prepared by a Pd-catalyzed Sonogashira coupling, leads to oxindoles (60-86% yields) [424],... 

The antibacterial agent sulfamethoxazole produced chlorinated and nonchlorinated DBFs when reacted with chlorine [91]. A ring-chlorinated product was formed via halogenation of the aniline moiety at sub-stoichiometiic concentrations of chlorine. 3-Amino-5-methylisoxazole, sulfate, and A-chloro-p-benzoquinone imine were formed via rupture of the sulfamethoxazole sulfonamide moiety at stoichiometric excess of chlorine. 

Sulfonamides undergo rearrangement in an analogous way. The aromatic ring can be aniline [152], carbazole [153], or indole [114], Some examples are outlined in Scheme 51. 

Over 5000 sulfonamides have been synthesized and tested. The physiologically active ones are known collectively as sulfa drugs. Most involve variations of groups in place of the hydrogens of the sulfonamide moiety. A general synthesis of these compounds is outlined. Aniline is... 

Quantitative stoichiometric gas-solid or solid-solid (these at 0 °C) acylations of amines with acid chlorides are varied (Scheme 32). However, for a clean reaction the liberated hydrochloric acid has to be neutralized by an additional gaseous or solid base that may also be a second mole of the amine. The reactions are performed in an evacuated flask or in a ball-mill, respectively. There are only minimal losses of the amides or sulfonamides upon removal of the stoichiometric coproduct with water [91]. The solid-solid reactions can be turned into sustainable 100% yield processes with optimal atom efficiency by milling stoichiometric 1 1 1 mixtures of acid chloride, aniline derivative, and K2CO3... 

The thiazetidine 163 has been specifically synthesized to give the openring structure 268 after treatment with aniline in acetone at — 78°C. 1,2-Thiazetidines (172) have been treated with Grignard reagents to yield sulfonamide sulfoxides. ... 

Sulfamethoxazole 4 - Amino -N- 5 -methyl-3 - isoxazolyl)benzene sulfonamide Sulfonylation of aniline, sulfphoamidation with 3-amino-5-methyl-isoxazol... 

The structure of sulfonamides is shown for representative purposes. Among the several thousand compounds in existence, about 25-30 have found widespread use. Sulfanilamide itself is, by present-day standards, very inactive. It was the development of heterocyclic derivatives that produced the highly potent sulfathiazole (9.90). When a succinyl or phthalyl group is attached to the aniline nitrogen, the inactive acylanilide derivatives will not be absorbed from the intestinal tract. Slow deacylation by intestinal... 

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