Recent developments in solid-phase organic synthesis

Brown, Richard C. D.

doi:10.1039/a805801f

Cited by 126 publications

(1 citation statement)

References 208 publications

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“…However, a high yield of desired product at each synthetic stage is particularly important for these methods [2], as various side reactions, lowering the chemical yield of the individual synthetic steps, are the main limitation of the method [3]. In order to make the method more efficient, a deeper understanding of these unwanted processes is desirable.…”

Section: Introductionmentioning

confidence: 99%

Oligomerization of Indole Derivatives with Incorporation of Thiols

et al. 2008

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Two molecules of indole derivative, e.g. indole-5-carboxylic acid, reacted with one molecule of thiol, e.g. 1,2-ethanedithiol, in the presence of trifluoroacetic acid to yield adducts such as 3-[2-(2-amino-5-carboxyphenyl)-1-(2-mercaptoethylthio)ethyl]-1H-indole-5-carboxylic acid. Parallel formation of dimers, such as 2,3-dihydro-1H,1'H-2,3'-biindole-5,5'-dicarboxylic acid and trimers, such as 3,3'-[2-(2-amino-5-carboxy-phenyl)ethane-1,1-diyl]bis(1H-indole-5-carboxylic acid) of the indole derivatives was also observed. Reaction of a mixture of indole and indole-5-carboxylic acid with 2-phenylethanethiol proceeded in a regioselective way, affording 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-1H-indole-5-carboxylic acid. An additional product of this reaction was 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-2,3-dihydro-1H,1'H-2,3'-biindole-5'-carboxylic acid, which upon standing in DMSO-d6 solution gave 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-1H,1'H-2,3'-biindole-5'-carboxylic acid. Structures of all compounds were elucidated by NMR, and a mechanism for their formation was suggested.

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Section: Introductionmentioning

confidence: 99%

Oligomerization of Indole Derivatives with Incorporation of Thiols

et al. 2008

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Polymer-assisted solution-phase (PASP) library synthesis of α-ketoamides

South

Dice

Parlow

2000

Biotechnol. Bioeng.

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A parallel solution‐phase library synthesis of α‐ketoamides is described. The two‐step library synthesis is accomplished using polymer‐assisted solution‐phase (PASP) synthesis techniques. This high‐yielding, multi‐step sequence utilizes sequestering resins for the removal of reactants, reactant by‐products, and tagged reagents. The first step of the library synthesis utilizes PASP resins to mediate the amide coupling of an α‐hydroxy acid with an amine. The second step uses PASP resins for the periodinane oxidation of the α‐hydroxy acid to an α‐ketoamide leaving highly pure products after simple filtration and evaporation. © 2000 John Wiley & Sons, Inc. Biotechnol Bioeng (Comb Chem) 71:51–57, 2000.

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Solid phase synthesis - designer linkers for combinatorial chemistry: a review

Gordon

Balasubramanian

1999

J. Chem. Technol. Biotechnol.

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Recent developments in solid-phase organic synthesis

Cited by 126 publications

References 208 publications

Oligomerization of Indole Derivatives with Incorporation of Thiols

Oligomerization of Indole Derivatives with Incorporation of Thiols

Polymer-assisted solution-phase (PASP) library synthesis of α-ketoamides

Solid phase synthesis - designer linkers for combinatorial chemistry: a review

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