http://www.if-pan.krakow.pl/pjp/pdf/2008/4_439.pdf

Tropane alkaloids as medicinally useful natural products and their synthetic derivatives as new drugs.

Green recipes to quinoline: A review

The efficient, regioselective synthesis of functionalized/annulated quinolines was achieved by the coupling of 2-aminoaryl ketones with alkynes/active methylenes/α-oxoketene dithioacetals promoted by InCl(3) in refluxing acetonitrile as well as under solvent-free conditions in excellent yields. This transformation presumably proceeded through the hydroamination-hydroarylation of alkynes, and the Friedlander annulation of active methylene compounds and α-oxoketene dithioacetals with 2-aminoarylketones. In addition, simple reductive and oxidative cyclization of 2-nitrobenzaldehyde and 2-aminobenzylalcohol, respectively, afforded substituted quinolines. Systematic optimization of the reaction parameters allowed us to identify two-component coupling (2CC) conditions that were tolerant of a wide range of functional groups, thereby providing densely functionalized/annulated quinolines. This approach tolerates the synthesis of various bioactive quinoline frameworks from the same 2-aminoarylketones under mild conditions, thus making this strategy highly useful in diversity-oriented synthesis (DOS). The scope and limitations of the alkyne-, activated methylene-, and α-oxoketene dithioacetal components on the reaction were also investigated.

InCl3‐Driven Regioselective Synthesis of Functionalized/Annulated Quinolines: Scope and Limitations

The cytotoxic properties and preferential toxicity to tumour cells displayed by some 2,4-bis(benzylidene)-8-methyl-8-azabicyclo[3.2.1] octan-3-ones and 3,5-bis(benzylidene)-1-methyl-4-piperidones.

The capture and storage of solar energy requires chromophores that absorb light throughout the solar spectrum. We report here the synthesis, characterization, electrochemical, and photophysical properties of a series of Ru(II) polypyridyl complexes of the type [Ru(bpy)2(N–N)]2+ (bpy = 2,2′-bipyridine; N–N is a bidentate polypyridyl ligand). In this series, the nature of the N–N ligand was altered, either through increased conjugation or incorporation of noncoordinating heteroatoms, as a way to use ligand electronic properties to tune redox potentials, absorption spectra, emission spectra, and excited state energies and lifetimes. Electrochemical measurements show that lowering the π* orbitals on the N–N ligand results in more positive Ru3+/2+ redox potentials and more positive first ligand-based reduction potentials. The metal-to-ligand charge transfer absorptions of all of the new complexes are mostly red-shifted compared to Ru(bpy)32+ (λmax = 449 nm) with the lowest energy MLCT absorption appearing at λ...

Controlling ground and excited state properties through ligand changes in ruthenium polypyridyl complexes.

Simple synthesis of quinolines and dibenzo[b,f][1,5]diazocines under microwave irradiation

Synthesis of 2,4-disubstituted nortropinone derivatives by aldol condensation

Benzodiazepines are interesting compounds because of their pharmacological properties. Many members of this family are, in fact, nowadays widely used as tranquilizing and anticonvulsant agents. Although the first benzodiazepine was introduced as a drug nearly 30 years ago, the research in this area is still very active and is directed towards the synthesis of compounds of enhanced pharmacological activity. Some benzodiazepine derivatives are also used in industry, such as in photography (as dyes for acrylic fibers), and also as anti-inflammatory agents. 1H-1,5Benzodiazepines are used as starting materials for the preparation of some fused ring benzodiazepine derivatives, such as triaxol and oxadiazol. Despite their wide range of pharmacological activity, industrial and synthetic application, the synthesis of 1H-1,5-benzodiazepines has received little attention. As a part of research program related to the synthetic study of pharmacologically interesting benzodiazepine compounds, herein we now report the synthesis of 1H-1,5-benzodiazepine derivatives with heteroaromatic ketones (2-acetylfuran 2a, 2-acetylthiophene 2b, 2-acetylpyridine 2c, 3-acetylpyridine 2d, and 4-acetylpyridine 2e) by using conc-HCl, SiO2, or polyphosphoric acid (PPA) (Scheme 1). Specially we report synthesis of quinoxaline derivatives with phenylenediamine 1a and acetylpyridines 2c, 2e in aqueous 10% conc-HCl solution (Scheme 2). Moreover we describe the structural analysis of 7-chloro2,2,4-trimethyl-2,3-dihydro-1H-1,5-benzodiazepine 3f and 8-chloro-2,2,4-trimethyl-2,3-dihydro-1H-1,5-benzodiazepine 3g synthesized by 4-chloro-1,2-phenylenediamine 1b with acetone. Earlier we reported the synthesis of 2,4,4,-trimethyl-3H-5hydro-1,5-benzodiazepine and 2,4-diphenyl-4-methyl-3H-5hydro-1,5-benzodiazepine by using various reagents instead of PPA. When 1a was treated with 2a in the presence of PPA at 4045 °C for 5 h, a yellow crystalline solid, 3a was isolated

Synthesis of 1H-1,5-Benzodiazepine Derivatives and Pyridinylquinoxalines with Heterocyclic Ketones

The tropane class of alkaloids has continued to elicit the unabated interests among organic chemists because of their pharmacological significance, and a great deal of efforts has been focused on the stereochemical synthetic methodologies. Cocaine, a notorious member of this alkaloidal family, is found in erythroxylon coca, indigenous to the higher elevations of peru. The natives of this region, descendants of the Incas, still chew the coca leaf for its stimulatory properties. In particular, a series of tropans showed anticonvulsant activity against pentylenetetrazolinduced convulsions in mice and antiarrhythmic activity in rabbit previously treated with ouabain. As a part of ongoing research for the pharmacologically interesting tropane compounds, herein we report a new synthetic conditions of corresponding 2-substituted 8-azabicyclo[3.2.1]octan-3-one, 3, by aldol condensation from 8substituted 8-azabicyclo[3.2.1]octan-3-one, 1. We already reported a synthesis of 2,4-disubstituted 8-azabicyclo[3.2.1]octan-3-one, 2, derived from the reaction of N-substituted 8azabicyclo[3.2.1]octan-3-one, 1, with aldehydes (R1CHO) in the presence of ethanol and aqueous 5 N NaOH. We also reported the synthesis of di-(N-tropinonyl)alkanes from the reaction of phenylenediamines (or diaminoalkanes) with 2,5-dimethoxytetrahydrofuran and acetonedicarboxylic acid. Then our attempt to prepare 2-substituted 8-azabicyclo[3.2.1]octan-3-one, 3, from 8-substituted 8-azabicyclo[3.2.1]octan-3-one, 1, was unsuccessful, under various reaction conditions: sodium hydride, sodium methoxide, or butyl lithium. But M. Majewski and R. Lazny reported that their synthesized compound, 2-benzylidene-8-methyl-8-azabicyclo[3.2.1]octan-3-one was done through three-step treatment of chiral lithium amide, Ac2O, and SiO2 (Scheme 1). In brief, as their synthetic method had three-step reactions and three times work-ups, it was so complicated. Recently, Peter A. Crooks et al. reported two-step synthesis by treatment of lithium diisopropylamide or lithium bis(trimethylsilyl)amide. In order to synthesize 2-substituted 8-azabicyclo[3.2.1]octan-3-one, 3, simply and efficiently, we conducted research on the effect of aqueous NaOH concentration variations (1 N, 0.5 N, 0.1 N, 0.02 N, or 0.01 N). Yield comparison of compound 3e according to concentration variation of aqueous NaOH solution is expressed in Table 1. In case of higher concentrations over aqueous 0.01 N NaOH solution, the ratio of 2,4-disubstituted 8-azabicyclo[3.2.1]octan-3-one, 2, was produced somewhat higher than that of 2-substituted 8-azabicyclo[3.2.1]octan-3-one, 3. Yield of 8-benzylidene-8-phenyl-8-azabicyclo[3.2.1]octan-

Synthesis of 2-Substituted 8-Azabicyclo[3.2.1]octan-3-ones in Aqueous NaOH Solution of Low Concentration

To develop a luminescent material with high color
purity, luminous efficiency, and stability, we synthesized diketone by
carbonylative Suzuki coupling in the presence of Pd(NHC) complex as the
catalyst. Carbonylative coupling of 4,4’-diiodobiphenyl and
phenylboronic acid was investigated to study in detail the catalytic ability of
the Pd(NHC) complex. Reactions were carried out using both CO and metal
carbonyls. Bis-(1,3-dihydro-1,3-dimethyl-2H-imidazol- 2-ylidene) diiodo
palladium was used as the catalytic complex. Reaction products biphenyl-4,4’-diylbis
(phenyl- methanone) 3 and (4’-iodobiphenyl-4-yl)(phenyl) methanone 4 were obtained as a result of CO
insertion into the palladium(II)-aryl bond. However, when
pyridine-4-yl boronic acid was used in place of phenylboronic acid as the
starting reagent, synthetic reaction yielding 3 and 4 were found not to occur.

https://file.scirp.org/pdf/GSC_2013022611271099.pdf

Do-Hun Lee

Papers

Simple synthesis of quinolines and dibenzo[b,f][1,5]diazocines under microwave irradiation

Synthesis of 2,4-disubstituted nortropinone derivatives by aldol condensation

Synthesis of 1H-1,5-Benzodiazepine Derivatives and Pyridinylquinoxalines with Heterocyclic Ketones

Synthesis of 2-Substituted 8-Azabicyclo[3.2.1]octan-3-ones in Aqueous NaOH Solution of Low Concentration

Carbonylative Coupling of 4,4’-Diiodobiphenyl Catalyzed by Pd(NHC) Complex