SUBSTITUTED 1,10-PHENANTHROLINES. VIII. 2- AND 3-PHENYL DERIVATIVES<sup>1</sup>

Case, Francis H.; Sasin, Richard

doi:10.1021/jo01127a006

Cited by 28 publications

(5 citation statements)

References 7 publications

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“…This compound was prepared according to a published procedure . Mp: 182−183 °C (benzene) (lit . mp 185−186 °C (benzene)).…”

Section: Methodsmentioning

confidence: 99%

Neutral and Cationic Iridium(I) Complexes Bearing Chiral Phenanthroline-Derived Benzimidazolylidenes: Synthetic, Structural, and Catalytic Studies

Metallinos

2009

Organometallics

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A series of neutral and cationic iridium(I) complexes bearing chiral and achiral phenanthroline-derived benzimidazolylidene ligands were synthesized and characterized. Spectroscopic and crystallographic data indicate that the principal plane of the NHC ligand in the achiral complexes is positioned orthogonally with respect to the Ir-Cl or Ir-P bonds, while the planes of NHC ligands in the corresponding chiral complexes are twisted by a torsion angle that depends on the size of the 2,9-substituents. All of the new complexes showed varying degrees of catalytic activity and enantioselectivity toward hydrogenation of acetamidoacrylates, with the best results being achieved using 2,9-diphenyl-substituted (S,S)-20a, which afforded (-)-(R)-methyl 2-acetamidopropanoate (12a) in 97% yield and 81% ee.

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“…This compound was prepared according to a published procedure . Mp: 182−183 °C (benzene) (lit . mp 185−186 °C (benzene)).…”

Section: Methodsmentioning

confidence: 99%

Neutral and Cationic Iridium(I) Complexes Bearing Chiral Phenanthroline-Derived Benzimidazolylidenes: Synthetic, Structural, and Catalytic Studies

Metallinos

2009

Organometallics

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“…Experimental procedures and analytical data for the synthesis of compounds 12 , 13a − d , 14 − 16 , 17b − d , m , n , p − u , 18b , d , e , 20 , 23 , 24 , 26 , 27 , 29c − e ; ,,− ,− analytical data for 17a , e − l , o , 18c , 21 , 29b , 30 , 31 ; X-ray crystallographic data and the procedure for the biochemical evaluation. This material is available free of charge via the Internet at .…”

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confidence: 99%

Design, Synthesis, and Evaluation in Vitro of Quinoline-8-carboxamides, a New Class of Poly(adenosine-diphosphate-ribose)polymerase-1 (PARP-1) Inhibitor

et al. 2008

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Poly(ADP-ribose)polymerase-1 is an important target enzyme in drug design; inhibitors have a wide variety of therapeutic activities. A series of quinoline-8-carboxamides was designed to maintain the required pharmacophore conformation through an intramolecular hydrogen bond. 3-Substituted quinoline-8-carboxamides were synthesized by Pd-catalyzed couplings (Suzuki, Sonogashira, Stille) to 3-iodoquinoline-8-carboxamide, an efficient process that introduces diversity in the final step. 2-Substituted quinoline-8-carboxamides were prepared by selective Pd-catalyzed couplings at the 2-position of 2,8-dibromoquinoline, followed by lithium-bromine exchange of the intermediate 2-(alkyl/aryl)-8-bromoquinolines and reaction with trimethylsilyl isocyanate. The intramolecular hydrogen bond was confirmed by X-ray and by NMR. The SAR of the 3-substituted compounds for inhibition of human recombinant PARP-1 activity showed a requirement for a small narrow group. Substituents in the 2-position increased potency, with the most active 2-methylquinoline-8-carboxamide having IC(50) = 500 nM (IC(50) = 1.8 microM for 5-aminoisoquinolin-1-one (5-AIQ, a standard water-soluble inhibitor)).

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“…The synthesis of functional derivatives of 1,10-phenanthrolines such as 8a,b, and 10 has not been studied extensively [12,13] although their 9-amino and 9-pyridyl derivatives display useful photoluminescence properties [14] and are ligands in chromogenic receptors [15,16]. Acetonitrile was used as the solvent in the latter case in light of the low solubility of aldimine 11 in toluene.…”

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Synthesis and oxidation of 2-furyl-4-R-substituted and furo[3,2-c]-condensed 1,2,3,4-tetrahydro-1,10-phenanthrolines and quinolines*

Zaitsev

Mikhailova

Orlova

et al. 2009

Chem Heterocycl Comp

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were obtained for the first time from 8-aminoquinolines using the Povarov reaction. Various oxidizing agents were shown to effect the elimination of the substituent at C(4) with subsequent aromatization of the tetrahydroquinoline fragment.The Povarov reaction (the acid-catalyzed [4+2] cycloaddition of electron-rich alkenes to N-arylazomethines) is commonly used for the synthesis of substituted tetrahydroquinolines and, judging from the rising number of publications, is now experiencing a rebirth of interest [1-3]. Nevertheless, there have been only a few examples of the preparation of 2-furyl-1,2,3,4-tetrahydroquinolines by this method [4][5][6] and there is only one example of the use of an 8-aminoquinoline in the Povarov reaction [7]. This paucity is related primarily to the acidophobic nature of the furan fragment and, secondarily, to passivation of the acid catalysts. The behavior of 2-furyltetrahydroquinolines in the presence of oxidizing agents has also not been studied extensively and apparently is complex.2 -Furyltetrahydroquinolines 2a,b, 3, and 4 used as the starting compounds in this work were obtained by the Povarov reaction from the corresponding furfurylideneanilines 1a,b and electron-rich alkenes (dihydrofuran, 3,4-2H-dihydropyran, and N-vinyl-2-pyrrolidone) in the presence of boron trifluoride etherate as described in our previous work [8]. The hydrogenated quinolines 2-4 are cis addition adducts.

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SUBSTITUTED 1,10-PHENANTHROLINES. VIII. 2- AND 3-PHENYL DERIVATIVES¹

Cited by 28 publications

References 7 publications

Neutral and Cationic Iridium(I) Complexes Bearing Chiral Phenanthroline-Derived Benzimidazolylidenes: Synthetic, Structural, and Catalytic Studies

Neutral and Cationic Iridium(I) Complexes Bearing Chiral Phenanthroline-Derived Benzimidazolylidenes: Synthetic, Structural, and Catalytic Studies

Design, Synthesis, and Evaluation in Vitro of Quinoline-8-carboxamides, a New Class of Poly(adenosine-diphosphate-ribose)polymerase-1 (PARP-1) Inhibitor

Synthesis and oxidation of 2-furyl-4-R-substituted and furo[3,2-c]-condensed 1,2,3,4-tetrahydro-1,10-phenanthrolines and quinolines*

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SUBSTITUTED 1,10-PHENANTHROLINES. VIII. 2- AND 3-PHENYL DERIVATIVES1

Cited by 28 publications

References 7 publications

Neutral and Cationic Iridium(I) Complexes Bearing Chiral Phenanthroline-Derived Benzimidazolylidenes: Synthetic, Structural, and Catalytic Studies

Neutral and Cationic Iridium(I) Complexes Bearing Chiral Phenanthroline-Derived Benzimidazolylidenes: Synthetic, Structural, and Catalytic Studies

Design, Synthesis, and Evaluation in Vitro of Quinoline-8-carboxamides, a New Class of Poly(adenosine-diphosphate-ribose)polymerase-1 (PARP-1) Inhibitor

Synthesis and oxidation of 2-furyl-4-R-substituted and furo[3,2-c]-condensed 1,2,3,4-tetrahydro-1,10-phenanthrolines and quinolines*

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SUBSTITUTED 1,10-PHENANTHROLINES. VIII. 2- AND 3-PHENYL DERIVATIVES¹