Stolle synthesis

Acid-catalyzed oxindole formation from aniline and a-chlorocarboxylic acid chloride. 

Przheval skii, N. M. Grandberg, 1.1. Khim. Geterotsikl. Soedin. 1982, 940. 

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Stolle synthesis. Formation of indole derivatives by the reaction of arylamines with a-haloacid chlorides or oxalyl chloride, followed by cyclization of the resulting amides with aluminum chloride. 

A related synthesis produces indolones by a different Friedel-Crafts route. The Stolle synthesis reacts with a secondary aryl amine such as diphenylamine with an a-chloro acid chloride or an a-bromo acid bromide to give an a-bromoamide (such as 315) or an a-chloroamide. An early version of the reaction used oxalyl chloride, but a more typical example is the reaction of 2-bromopropanoyl bromide with 314 to give 315. Friedel-Crafts cyclization (with AICI3) led to the indolone 316.1 ... 

Amides can also be obtained by AICI3 catalyzed ester amine exchange which proceeds primarily without racemization of chiral centers (eq 24). The reaction of phenols with /3-keto esters is known as the Pechmann condensation (eq 25). Aryl amines are used in the Riehm quinoline synthesis (eq 26) Aromatic systems may be coupled via the Scholl reaction (eq 27) and indole derivatives are prepared in the Stolle synthesis (eq 28). In the Zincke-Suhl reaction, phenols are converted to dienones (eq 29). 3 ... 

HINSBERG - STOLLS Indoie-OxindoiaSynthesis indoie synthesis Irom anilines and glyoxal (Hinsberg), oxindola synthesis from anilines and a haloacyi hafides (Stolie). 

The elegant synthesis of sodium azide from hydrazine and alkyl nitrite is carried out in the same way (Stolle) ... 

Another interesting example is the synthesis of 77-(2-thiazolyl)-nortropinon 121. Stoll and co-authors [175] described the synthesis of this drug-like product via the legendary first total synthetic approach proposed by Robinson in 1917 [176] for the natural alkoloid tropinone, also well known as a good example of biomimetic reaction. In this tandem treatment, 2-aminothiazole was reacted with succinaldehyde and acetonedicarboxylic acid yielding 77-(2-thiazolyl)-nortropinon 121 in moderate yields (Scheme 58). 

Synthesis of Heterocycles with a Variable Number of Atoms , R. Delaby and R. Damiens, in Festschrift Arthur Stoll , Birkhauser, Basel, 1957, p. 474. 

The synthesis of compd VI, already mentioned, was described earlier by Stoll Scher-rer (Ref 2) and Dilthey et al (Ref 4). The synthesis of Cyclohexanone Monoperoxide,... 

Many methods have been developed for the preparation of carbides and nitrides, and these will be described in this section. General references are Schwarzkopf and Kieffer,24 Juza,25 Storms,26 Toth,27 Benesovsky, Kieffer and Ettmayer,28 Santhanam,29 and Stoll and Santhanam.30 Kosolapova31 and Frad32 provide a detailed description of the element-by-element synthesis of carbides, covering the period prior to 1971. 

G. T. Wang, S. Wang, R. Gentles, T. Sowin, C. J. Maring, D. J. Kempf, W. M. Kati, V. Stoll, K. D. Stewart, and G. Laver, Design, synthesis, and structural analysis of inhibitors of influenza neuraminidase containing a 2,3-disubstituted tetrahydrofuran-5-carboxylic acid core,... 

Kahweofuran (2-methyl-3-oxa-8-thiabicyclo(3.3.0)-1.4-octadiene, 8 ) was first isolated by Stoll et al. (19) and its structure later confirmed by synthesis (3J ). This compound possesses a roasty/sulfury-note as do the related ethyl- and dimethyl derivatives are unique to coffee. So far, the ethyl and dimethyl compounds have not been detected in the roasted foods or in monosaccharide/cysteine model experiments. 

Liver cell swelling not only inhibits proteolysis, but also stimulates protein synthesis. In sharp contrast, cell shrinkage stimulates proteolysis but inhibits protein synthesis (Stoll et al., 1992). That cell hydration affects both protein degradation and synthesis in opposite directions is a finding that has a direct bearing on the problem of protein-catabolic states in disease (see p. 204). 

Stoll, B., Gerok, W., Lang, F Haussinger, D. (1992). Liver cell volume and protein synthesis. Biochem. J. 287,217-222. 

Grota, J., Domke, I., Stoll, I., Schroder, T., Mattay, J., Schmidtmann, M., Bogge, H., and Muller, A. (2005) Synthesis, fragmentation, and rearrangement reactions of annelated cyclobutyl-carbinols. Synthesis, 2321-2326. 

An improved synthesis of dihydrolysergic acid, which yielded the homogeneous racemates and furthermore led to the optically active dihydrolysergic acids, was effected via racemic dihydronorlysergic acids (54). As a starting material for this novel synthesis, Stoll and Rutschmann used the quinolone XXIII which had already been described by Gould and Jacobs (55). 

As the resolution of the racemic lysergic acid into its optical antipodes and the synthesis of ergometrine had been described earlier by Stoll and Hofmann (25, 66), this meant that not only had the synthesis of d-lysergic acid been achieved but also the first total synthesis of an ergot alkaloid. 

The synthesis of 1-methyli satin by the method of Stolle, using... 

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