Kombinatorische Festphasensynthese strukturell komplexer Thiazolylhydantoine

Stadlwieser, Josef; Ellmerer-Müller, Ernst P.; Takó, Andreas; Maslouh, Najib; Bannwarth, Willi

doi:10.1002/(sici)1521-3757(19980518)110:10<1487::aid-ange1487>3.0.co;2-7

Cited by 10 publications

(2 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Examples include benzazepinones, [262] benzodiazepinones, [258,263] diazepindiones, [264±266] hydantoins, [258, 263, 267±274] thiohydantoins, [268] thiazolylhydantoins, [275] benzopyrones, [276] benzoisothiazolones, [258] benzisoxazoles, [277,278] diketopiperazines, [265, 279±281] diketomorpholines, [280] quinazolindiones, [282,283] hydroxyquinolinones, [284] pyrazolones, [285±287] dihydropyridines, [288] dihydropyrimidindiones, [289] pyridine-fused heterocycles, [290] oxazines, [291,292] oxazolines, [291,292] oxazolidinones, [293±296] phthalides, [297] lactones, [298±300] lactams, [301] cyclic sulfonamides, [302] cyclic ethers, [303±306] cyclic imides, [307] tetrahydro-b-carbolines, [308,309] 2-quinolone, [310] coumarin, [310] indolyl diketopiperazine alkaloids, [311,312] and cyclic peptides. Examples include benzazepinones, [262] benzodiazepinones, [258,263] diazepindiones, [264±266] hydantoins, [258, 263, 267±274] thiohydantoins, [268] thiazolylhydantoins, …”

Section: Cyclative Cleavagementioning

confidence: 99%

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Tzschucke

Märkert

Bannwarth

et al. 2002

Angew. Chem. Int. Ed.

Self Cite

339

133

View full text Add to dashboard Cite

The shift of paradigm in combinatorial chemistry, from large compound libraries (of mixtures) on a small scale towards defined compound libraries where each compound is prepared in an individual well, has stimulated the search for alternative separation approaches. The key to a rapid and efficient synthesis is not only the parallel arrangement of reactions, but simple work-up procedures so as to circumvent time-consuming and laborious purification steps. During the initial development stages of combinatorial synthesis it was believed that rational synthesis of individual compounds could only be achieved by solid-phase strategies. However, there are a number of problems in solid-phase chemistry: most notably there is the need for a suitable linker unit, the limitation of the reaction conditions to certain solvents and reagents, and the heterogeneous reaction conditions. Further disadvantages are: the moderate loading capacities of the polymeric support and the limited stability of the solid support. In the last few years several new separation techniques have been developed. Depending on the chemical problem or the class of compounds to be prepared, one can choose from a whole array of different approaches. Most of these modern separation approaches rely on solution-phase chemistry, even though some of them use solid-phase resins as tools (for example, as scavengers). Several of these separation techniques are based on liquid-liquid phase separation, including ionic liquids, fluorous phases, and supercritical solvents. Besides being benign with respect to their environmental aspects, they also show a number of advantages with respect to the work-up procedures of organic reactions as well as simplicity in the isolation of products. Another set of separation strategies involves polymeric supports (for example, as scavengers or for cyclative cleavage), either as solid phases or as soluble polymeric supports. In contrast to solid-phase resins, soluble polymeric supports allow reactions to be performed under homogeneous conditions, which can be an important factor in catalysis. At the same time, a whole set of techniques has been developed for the separation of these soluble polymeric supports from small target molecules. Finally, miscellaneous separation techniques, such as phase-switchable tags for precipitation by chemical modification or magnetic beads, can accelerate the separation of compounds in a parallel format.

show abstract

Section: Cyclative Cleavagementioning

confidence: 99%

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Tzschucke

Märkert

Bannwarth

et al. 2002

Angew. Chem. Int. Ed.

Self Cite

339

133

View full text Add to dashboard Cite

show abstract

“…Eine Vielzahl von Heterocyclen wurde durch polymergestützte Ansätze mit cyclisierender Abspaltung synthetisiert. Beispiele umfassen Benzazepinone,262 Benzodiazepinone,258, 263 Diazepindione,264–266 Hydantoine,258, 263, 267–274 Thiohydantoine,268 Thiazolylhydantoine,275 Benzopyrone,276 Benzisothiazolone,258 Benzisoxazole,277, 278 Diketopiperazine,265, 279–281 Diketomorpholine,280 Chinazolindione,282, 283 Hydroxychinolinone,284 Pyrazolone,285–287 Dihydropyridine,288 Dihydropyrimidindione,289 pyridinanellierte Heterocyclen,290 Oxazine,291, 292 Oxazoline,291, 292 Oxazolidinone,293–296 Phthalide,297 Lactone,298–300 Lactame,301 cyclische Sulfonamide,302 cyclische Ether,303–306 cyclische Imide,307 Tetrahydro‐β‐carboline,308, 309 2‐Chinolon,310 Cumarin,310 Indolyldiketopiperazin‐Alkaloide311, 312 und cyclische Peptide 313–315. Auch lichtinduzierte cyclisierende Abspaltungen sind beschrieben 310, 316…”

Section: Polymergestützte Trenn‐ Und Reinigungsverfahrenunclassified

Moderne Trennverfahren zur effizienten Aufarbeitung in der organischen Synthese

et al. 2002

Self Cite

View full text Add to dashboard Cite

Die kombinatorische Synthese [1,2] wird als eine der Schl¸s-seldisziplinen f¸r den konstanten Nachschub an chemischen Verbindungen angesehen, die auf biologische Aktivit‰t gegen¸ber der immens wachsenden Zahl biologischer Zielmolek¸le getestet werden kˆnnen. Zusammen mit dem Hochdurchsatz-Screening und einem effizienten Datenmanagement wird ihre Anwendung den Prozess der Wirkstoffentdeckung zweifelsohne beschleunigen. Urspr¸nglich konzentrierte sich die Kombinatorische Chemie auf die schnelle Synthese von hochkomplexen Gemischen mit winzigen An-

show abstract

Stereoselektive Festphasensynthese von β-Lactamen – ein neuartiger Zugang zu 1-Oxacephamen durch eine Ringschlußreaktion bei gleichzeitiger Abspaltung von der festen Phase

et al. 1999

View full text Add to dashboard Cite

Trotz der antibiotischen Aktivität und daher hohen Attraktivität von β‐Lactamen sind Festphasensynthesen für diese Verbindungsklasse bisher kaum entwickelt worden. Jetzt gelang die diastereoselektive Synthese des 1‐Oxacephams 2 aus dem harzgebundenen β‐Lactamderivat 1, das in fünf Stufen aus käuflichem Wang‐Harz zugänglich ist. Attraktiv sind die Synthesen von 2 und einem weiteren 1‐Oxacepham vor allem wegen der guten Ausbeuten, der hohen Reinheit der Produkte und der einfachen Durchführbarkeit der Reaktionssequenzen.

show abstract

Kombinatorische Festphasensynthese strukturell komplexer Thiazolylhydantoine

Cited by 10 publications

References 19 publications

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Moderne Trennverfahren zur effizienten Aufarbeitung in der organischen Synthese

Stereoselektive Festphasensynthese von β-Lactamen – ein neuartiger Zugang zu 1-Oxacephamen durch eine Ringschlußreaktion bei gleichzeitiger Abspaltung von der festen Phase

Contact Info

Product

Resources

About