- Catalytic Reductive Synthesis and Direct Derivatization of Unprotected Aminoindoles, Aminopyrroles, and Iminoindolines
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A titanium(III)-catalyzed radical cyclization to unprotected 3-aminoindoles, 3-aminopyrroles, or 3-iminoindolines is reported. The reaction is non-hazardous, scalable, and allows facile isolation of the free products by extraction. The method is demonstrated on a large substrate scope and it further allows the direct installation of various nitrogen protecting groups or the synthesis of building blocks for peptide chemistry in a single sequence. Fused bisindoles can be directly accessed from the cyclization products.
- Leijendekker, Leonardus H.,Weweler, Jens,Leuther, Tobias M.,Streuff, Jan
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supporting information
p. 6103 - 6106
(2017/05/22)
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- Copper-catalyzed oxidative ring closure of ortho-cyanoanilides with hypervalent iodonium salts: Arylation-ring closure approach to iminobenzoxazines
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A novel, highly modular synthetic methodology with high functional group tolerance was developed for the construction of iminobenzoxazine derivatives from ortho-cyanoanilides and diaryliodonium triflates via an oxidative arylation-cyclization path. The reaction is supposed to involve the formation of highly active aryl-copper(III) species. In this novel transformation, copper(II) triflate was used as catalyst in 1,2-dichloroethane or ethyl acetate and the reaction takes place at 75 °C in 2-16 h.
- Aradi, Klra,Novk, Zoltn
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supporting information
p. 371 - 376
(2015/03/05)
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- Diverse tandem cyclization reactions of o -cyanoanilines and diaryliodonium salts with copper catalyst for the construction of quinazolinimine and acridine scaffolds
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Two cyclization modes are realized to produce different nitrogen-containing heterocycles, i.e.; quinazolin-4(3H)-imines and acridines by assembling o-cyanoanilines and diaryliodonium salts via tandem reaction pathways.
- Pang, Xinlong,Chen, Chao,Su, Xiang,Li, Ming,Wen, Lirong
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supporting information
p. 6228 - 6231
(2015/01/09)
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- INDOLE CARBOXAMIDE DERIVATIVES AND USES THEREOF
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A compound of Formula (I) is provided that has been shown to be useful for treating a disease, disorder or syndrome that is mediated by the transportation of essential molecules in the mmpL3 pathway: (I) wherein R1, R2, R3, R4, R5 and R6 are as defined herein.
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Page/Page column 34
(2014/03/26)
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- Rhodium-catalyzed asymmetric hydrogenation of β-acetylamino acrylonitriles
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The rhodium-catalyzed asymmetric hydrogenation of β-acetylamino acrylonitriles was investigated by using monophosphine and bisphosphine ligands. It was found that an Rh-QuinoxP complex exhibited high enantioselectivities for β-aryl substituted β-acetylamino acrylonitriles and the Rh-JosiPhos CyPF-t-Bu complex was proven to be effective for the hydrogenation of tetrasubstituted olefins from cyclic β-acetylamino acrylonitriles.
- Ma, Miaofeng,Hou, Guohua,Wang, Junru,Zhang, Xumu
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experimental part
p. 506 - 511
(2011/06/17)
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- MODULATION OF CHEMOSENSORY RECEPTORS AND LIGANDS ASSOCIATED THEREWITH
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The present invention provides screening methods for identifying modifiers of chemosensory receptors and their ligands, e.g., by determining whether a test entity is suitable to interact with one or more interacting sites within the Venus flytrap domains of the chemosensory receptors as well as modifiers capable of modulating chemosensory receptors and their ligands.
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Page/Page column 59
(2009/01/20)
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- Synthesis and microbial transformation of β-amino nitriles
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Rhodococcus equi A4, Rhodococcus erythropolis NCIMB 11540 and Rhodococcus sp. R312 were investigated towards their ability to produce β-amino amides and acids from β-amino nitriles. The microorganisms show comparable trends: five-membered alicyclic 2-amino nitriles were transformed significantly faster than the six-membered compounds and the products of trans-2-amino nitriles (amides and acids) were formed considerably faster than the cis-counterparts (amides). The trans-five membered nitriles gave the amides (1b, 5b) in excellent enantiomeric excess (94-99%), the biotransformation of trans-six membered substrates resulted in the formation of the acid (3c, 7c) in excellent ee (87-99%). The ee's of the cis-compounds were throughout lower. Fifteen new substances were synthesized and characterized in the course of this work.
- Winkler, Margit,Martínková, Ludmila,Knall, Astrid C.,Krahulec, Stefan,Klempier, Norbert
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p. 4249 - 4260
(2007/10/03)
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- Preparation of enantiopure ketones and alcohols containing a quaternary stereocenter through parallel kinetic resolution of β-keto nitriles
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Racemic 1-methyl-2-oxocycloalkanecarbonitriles have been subjected to bioreduction by the fungus Mortierella isabellina NRRL 1757 through a parallel kineticresolution process. The u and l alcohols thus obtained (up to >99% ee) were easily separated and oxidized to the R and S ketones, respectively. The process can be then repeated so that both enantiomers of the ketone and two epimers of the alcohol can be obtained in their enantiopure forms.
- Dehli, Juan R.,Gotor, Vicente
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p. 1716 - 1718
(2007/10/03)
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- Polycyclic compounds
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PCT No. PCT/GB96/02945 Sec. 371 Date Aug. 25, 1998 Sec. 102(e) Date Aug. 25, 1998 PCT Filed Nov. 28, 1996 PCT Pub. No. WO97/19929 PCT Pub. Date Jun. 5, 1997Compounds of Formula (I), methods for their preparation, pharmaceutical formulations and use thereof.
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- The synthesis of pyrido[3,2-a]acridines
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6-Aminoquinoline (5) reacts with 2-cyanocyclohexanone (6a) or ethyl 2-oxocyclohexanecarboxylate (6b) to give enamines which can be cyclised, under Lewis acid catalysed conditions, to tetrahydropyrido[3,2-a]acridines (9, 13). Dehydrogenation of these tetra
- Groundwater, Paul W.,Munawar, Munawar Ali
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p. 2463 - 2469
(2007/10/03)
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- The synthesis and assay of radiolabelled benzene derivatives
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Several new syntheses of 1- and 4-[14C]anisole have been investigated and routes from [14C]cyanide and from 2-[14C]acetone are described which are better than those previously reported. The key step in one of the syntheses was catalytic dehydrogenation of 1-[14C]cyclohexanone to 1-[14C]phenol. Degradation of 5,6,7,8-tetrachloro-3,4-dihydro-1,4-etheno-[14C]naphthalen-2-(1H)-on e (10) prepared from [14C]anisole and tetrachlorobenzene has shown that the key step had proceeded without scrambling of the label.
- Hales, Neil J.,Heaney, Harry,Hollinshead, John H.,Ley, Steven V.
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p. 7741 - 7754
(2007/10/02)
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- Anxiolytic properties of certain annelated [1,2,3]triazolo[1,5-c]pyrimidin-5(6H)-ones
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Modification of the benzodiazepine (BZ) receptor binding template 2-aryl[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one by replacement of the annelated benzene ring with various alicyclic and heterocyclic moieties led to novel structures with potent BZ receptor binding affinity. High affinity was found in some cycloalkyl-annelated [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones and in some 7,8,9,10-tetrahydropyrido[3,4-e][1,2,4]triazolo[1,5-c] pyrimidin-5(6H)-ones, in which the degree of activity was strongly dependent on the N-substituent in the 9-position. Nine compounds with BZ receptor IC50 binding affinity values equal or superior to diazepam were evaluated in secondary screening. One of these, 9-benzyl-2-phenyl-7,8,9,10-tetrahydropyrido[3,4-e] [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one, showed good activity in rats as a potential anxiolytic agent without sedative liability. However, it increased the rotorod deficit produced by ethanol at anxiolytic doses, an indication of alcohol interaction. Thus, none of the compounds showed an advantage over CGS 9896 (Yokoyama et al. J. Med. Chem. 1982, 25, 337-339), which is free of sedative and alcohol interaction potential as measured by the test procedures described.
- Francis,Bennett,Hyun,Rovinski,Amrick,Loo,Murphy,Neale,Wilson
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p. 2899 - 2906
(2007/10/02)
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