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Molecules, Volume 10, Issue 3 (March-May 2005) – 7 articles , Pages 516-582

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268 KiB  
Article
Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3β,17β-diol
by Eunsook Ma and Eunjeong Kim
Molecules 2005, 10(3), 572-582; https://doi.org/10.3390/10030572 (registering DOI) - 25 May 2005
Cited by 12 | Viewed by 9965
Abstract
Dehydroepiandrosterone (DHEA) reacted with m-chloroperoxybenzoic acid(m-CPBA) to form 3β-hydroxy-5α,6α-epoxyandrostan-17-one (1), but it did not reactwith 30% H2O2. 1,4,6-Androstatrien-3,17-dione (2) was obtained from DHEA and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in dioxane. Compound 2 was reacted with 30%H2O2 and 5% NaOH [...] Read more.
Dehydroepiandrosterone (DHEA) reacted with m-chloroperoxybenzoic acid(m-CPBA) to form 3β-hydroxy-5α,6α-epoxyandrostan-17-one (1), but it did not reactwith 30% H2O2. 1,4,6-Androstatrien-3,17-dione (2) was obtained from DHEA and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in dioxane. Compound 2 was reacted with 30%H2O2 and 5% NaOH in methanol to give 1α,2α-epoxy-4,6-androstadien-3,17-dione (3),which was stereoselectively reduced with NaBH4 to form 1α,2α-epoxy-4,6-androstadien-3β,17β-diol (7) and reacted with Li metal in absolute ethanol-tetrahydrofuran mixture togive 2-ethoxy-1,4,6-androstatrien-3,17-dione (8). Compound 2 was also epoxidized withm-CPBA in dichloromethane to afford 6α,7α-epoxy-1,4-androstadien-3,17-dione (4),which was reacted with NaBH4 to synthesize 6α,7α-epoxy-4-androsten-3β,17β-diol (9).Compound 4 was reduced with Li metal in absolute ethanol-tetrahydrofuran mixture toform 7β-ethoxy-6α-hydroxy-1,4-androstadien-3,17-dione (10). Compound 2 was reducedwith NaBH4 in absolute ethanol to form 4,6-androstadien-3β,17β-diol (5), which wasreacted with 30% H2O2 to give the original compound, but which reacted with m-CPBAto give 4β,5β-epoxy-6-androsten-3β,17β-diol (6). Full article
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54 KiB  
Article
Functionalization of 6-Nitrobenzo[1,3]dioxole with Carbonyl Compounds via TDAE methodology
by Ouassila Amiri-Attou, Thierry Terme and Patrice Vanelle
Molecules 2005, 10(3), 545-551; https://doi.org/10.3390/10030545 (registering DOI) - 13 May 2005
Cited by 41 | Viewed by 7222
Abstract
We report herein the synthesis of substituted 2-(6-nitrobenzo[1,3]dioxol-5-yl)-1- aryl ethanols and 2-(6-nitrobenzo[1,3]dioxol-5-yl)-propionic acid ethyl esters from the reaction of 5-chloromethyl-6-nitrobenzo[1,3]dioxole with various aromatic carbonyl and α- carbonyl ester derivatives using the tetrakis(dimethylamino)ethylene (TDAE) methodology. Full article
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230 KiB  
Article
Thermal Behaviour, Biological Activity and Conformational Study of a [Methoprene/β-Cyclodextrin] Complex in a Smoke Generating Formulation
by Paola González Audino, Hector Masuh and Eduardo Zerba
Molecules 2005, 10(3), 534-544; https://doi.org/10.3390/10030534 (registering DOI) - 13 May 2005
Cited by 3 | Viewed by 10766
Abstract
Methoprene, an insect growth regulator, was complexed with β-cyclodextrin, yielding a stable inclusion complex. TGA, X-ray powder diffraction and conformational analysis have been used to confirm the nature of this inclusion complex. The interaction between methoprene and β-cyclodextrin was investigated by means of [...] Read more.
Methoprene, an insect growth regulator, was complexed with β-cyclodextrin, yielding a stable inclusion complex. TGA, X-ray powder diffraction and conformational analysis have been used to confirm the nature of this inclusion complex. The interaction between methoprene and β-cyclodextrin was investigated by means of Molecular Mechanics. The results account for the formation of a 1:1 inclusion complex stabilised by Van der Waals forces and hydrogen bonds. The [methoprene–β-cyclodextrin] complex included in smoke generating formulations and protected from thermal decomposition by the foaming agent azodicarbonamide was shown to be stable enough to release methoprene in fumes with good yields. The improved stabilty of the methoprene complex showed a correlation with increased biological activity against Musca domestica. Full article
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348 KiB  
Article
Investigations on the Formation of 4-Aminobicyclo[2.2.2]-octanones
by Werner Seebacher, Dietmar Kröpfl, Ferdinand Belaj, Robert Saf, Antje Hüfner and Robert Weis
Molecules 2005, 10(3), 521-533; https://doi.org/10.3390/10030521 (registering DOI) - 13 May 2005
Cited by 3 | Viewed by 8270
Abstract
Benzylidene acetone reacts with thiocyanates derived from secondary amines in a one-pot reaction to give 4-aminobicyclo[2.2.2]octan-2-ones. The reaction mixture was investigated for the presence of possible intermediates using GC-MS. These intermediates – diketones and enamines – were prepared and exposed to the same [...] Read more.
Benzylidene acetone reacts with thiocyanates derived from secondary amines in a one-pot reaction to give 4-aminobicyclo[2.2.2]octan-2-ones. The reaction mixture was investigated for the presence of possible intermediates using GC-MS. These intermediates – diketones and enamines – were prepared and exposed to the same reaction conditions to examine the reaction mechanism. The reaction of ethyl styryl ketone with thiocyanates of secondary amines yielded cyclohexanone derivatives instead of the expected bicyclo- octanones. Their structures were established by means of a single crystal structure analysis. Full article
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79 KiB  
Article
A Novel Aromatic Iodination Method, with Sodium Periodate Used as the Only Iodinating Reagent
by Piotr Luliński, Maciej Sosnowski and Lech Skulski
Molecules 2005, 10(3), 516-520; https://doi.org/10.3390/10030516 (registering DOI) - 13 May 2005
Cited by 8 | Viewed by 9709
Abstract
Benzene, halobenzenes and some deactivated arenes readily reacted inanhydrous NaIO4/AcOH/Ac2O/concd. H2SO4 mixtures to afford, after quenching withexcess aqueous Na2SO3 solution (a reducing agent), purified iodinated products in 27-88% yields. This novel method of aromatic iodination is simple, fairly effective andenvironmentally safe. Full article
317 KiB  
Article
Experimental and Theoretical Studies on the Functionalization Reactions of 4-Benzoyl-1,5-Diphenyl-1H-Pyrazole-3-Carboxylic Acid and Acid Chloride with 2,3-Diaminopyridine
by Ismail Yıldırım, Fatma Kandemirli and Elif Demir
Molecules 2005, 10(3), 559-571; https://doi.org/10.3390/10030559 (registering DOI) - 31 Mar 2005
Cited by 18 | Viewed by 8316
Abstract
The 1H-pyrazole-3-carboxylic acid 2 was converted in good yield (69%) into the corresponding 1H-pyrazole-3-carboxamide 5 via reaction of the acid chloride 3 with 2,3- diaminopyridine (4). A different product, the 3H-imidazo[4,5-b] pyridine derivative 6, was formed from the reaction of 3 with 4 [...] Read more.
The 1H-pyrazole-3-carboxylic acid 2 was converted in good yield (69%) into the corresponding 1H-pyrazole-3-carboxamide 5 via reaction of the acid chloride 3 with 2,3- diaminopyridine (4). A different product, the 3H-imidazo[4,5-b] pyridine derivative 6, was formed from the reaction of 3 with 4 and base in benzene for 5 hours. The structures of the synthesized compounds were determined spectroscopically. The mechanism of the reaction between 3 and 4 was examined theoretically. Full article
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101 KiB  
Article
Synthesis of Some Phenylpropanoid Monoglycerides via the Mitsunobu Protocol
by Daniela I. Batovska, Takao Kishimoto, Vassya S. Bankova, Zornitsa G. Kamenarska and Makoto Ubukata
Molecules 2005, 10(3), 552-558; https://doi.org/10.3390/10030552 (registering DOI) - 31 Mar 2005
Cited by 22 | Viewed by 9324
Abstract
Natural monoglycerides of cinnamic, ferulic and p-coumaric acids were synthesized in good to high overall yields from isopropylidene glycerol via the Mitsunobu reaction and further deprotection of the corresponding acetonides with Amberlyst 15. The method avoids the need of protection of the phenolic [...] Read more.
Natural monoglycerides of cinnamic, ferulic and p-coumaric acids were synthesized in good to high overall yields from isopropylidene glycerol via the Mitsunobu reaction and further deprotection of the corresponding acetonides with Amberlyst 15. The method avoids the need of protection of the phenolic hydroxyls. During the Mitsunobu esterifications a strong influence of the acid strength on the efficacy and outcome of the reaction was observed. Full article
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