67522-88-7

Upstream product

• 64-67-5 diethyl sulfate 
• 25365-71-3 2-phenyl-1H-indol-3-carboxaldehyde 
• 948-65-2 2-phenyl-indole 
• 75-03-6 ethyl iodide 
• 68-12-2 N,N-dimethyl-formamide 
• 74-96-4 ethyl bromide 
• 13228-39-2 1-ethyl-2-phenyl-1H-indole 
• 298-12-4 Glyoxilic acid 

Downstream Products

• 1345510-09-9 5-(1-ethyl-2-phenyl-1H-indol-3-ylmethylene)pyrimidine-2,4,6-trione 
• 917207-80-8 1-ethyl-2-phenyl-1H-indole-3-carbonitrile 
• 239108-88-4 methyl 2-(3-1H-indolyl)-4-nitro-3-(2-phenylindol-3-yl)butanoate 

Relevant academic research and scientific papers

Selective nickel-catalyzed dehydrogenative-decarboxylative formylation of indoles with glyoxylic acid

Herein we present a new strategy for the dehydrogenative-decarboxylative coupling of indoles with glyoxylic acid. A broad range of indoles were transformed into the corresponding 3-formylindoles in moderate to good yields and excellent functional group tolerance. Notably, no N-formylation product was detected under our conditions.

Synthesis, single crystal X-ray studies and antimicrobial activities of novel Indole barbiturates

A novel series of N-substituted 2-phenyl indole derivatives incorporating barbituric acid have been synthesised and the chemical structures of the resulting molecules were characterised by means of IR, NMR and mass spectra. The antimicrobial activities of these compounds were investigated. Significant improvement in the antimicrobial activity can be achieved, in the presence of Cl and Br substituents on phenacyl moiety at para position. Single crystal X-ray analysis was also performed for the compound 6b in order to determine the crystal structure. Springer Science+Business Media, LLC 2011.

Synthesis of pyrrolidin-2-ones and of staurosporine aglycon (K-252c) by intermolecular Michael reaction

Indolo[2,3-a]pyrrolo[3,4-c]carbazoles were isolated from nature, e.g., from low plants, especially fungi, as structurally rare natural substances. Responsible for naming and also the most important representative of this type is staurosporine (1), isolated from Streptomyces staurosporeus, and its aglycon (2), also known as staurosporinone or K-252c. 3,4-Disubstituted pyrrolidin-2-ones, a group of compounds with many interesting biological properties are related to staurosporinone. The most important property is the inhibition of protein kinase C (PKC), so that this antiproliferative agent can interfere with the cell cycle. The synthetic strategy, developed by us, allows the synthesis of pyrrolidin-2-ones by an intermolecular Michael addition, starting from nitroethene derivatives and substituted acetate Michael donors. With this method also enantioselective syntheses can be carried out using chiral auxiliaries. After reduction of the nitro group and subsequent lactamization, the lactam partial structure, which is essential for the biological activity, is obtained. Besides indole substituents, which were used for the synthesis of staurosporinone, substituted indole-, phenyl- , and pyridyl- as well as enantiomerically pure (S)-proline derivatives were used. Here, considerably high diastereoselectivity and enantioselectivity ((S)-pyrrolidine) could be detected. Just like the total synthesis of staurosporinone within three steps, the easiest and shortest approach reported up to now, with good to moderate yields, this sequence allows highly diastereoselective syntheses, which open the easy access to a new family of compounds.

3-(substituted phenyl)phthalides

Process comprises the combination of the three steps of condensing 3-N(R)2 -4-X-benzoic acid with an aromatic or heterocyclic aldehyde, Y-CHO, under acidic conditions to produce 3-Y-5-X-6-N(R)2 phthalide (II), condensing said phthalide with a compound of the formula Z-H under alkaline or acid conditions to produce 2-(α-Y-α-Z)methyl-4-X-5-N(R)2 benzoic acid (III), and oxidizing said benzoic acid to produce 3-Y-3-Z-5-X-6-N(R)2 phthalide (I) where: R is hydrogen, non-tertiary alkyl of one to four carbon atoms, benzyl or substituted benzyl; X is hydrogen or halo; Y is 4-R1 -3-R2 -2-R1 -phenyl, 1-R5 -2-R6 -5/6-R4 -3-indolyl, 9-R7 -3-carbazolyl, 9-julolidinyl, 3,4-dioxymethylenephenyl, 2-thienyl, 1-R8 -2-pyrrolyl, or 4-pyridinyl; and Z is 4-R1 -3-R2 -2-R1 -phenyl, 1-R5 -2-R6 -5/6-R4 -3-indolyl or 1-R8 -2-pyrrolyl which are useful as colorless precursor color formers in carbonless duplicating and in thermal marking systems. The intermediates, 3-Y-5-X-6-N(R)2 phthalides (II) and 2-(α-Y-α-Z)methyl-4-X-5-N(R)2 benzoic acids (III) also have utility as colorless precursor color formers in carbonless duplicating and thermal marking systems.

Novel compounds, processes and marking systems

Mono and bis substituted (arylsulfonyl)alkanes useful as color formers, particularly in carbonless duplicating and thermal marking systems, are prepared by the interaction of the appropriate aldehyde or dialdehyde with the appropriate aryl or heterocyclic moiety and the appropriate phenylsulfinic acid in the presence of a catalyst.