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Molecules, Volume 7, Issue 2 (February 2002), Pages 104-319

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Research

Jump to: Review

Open AccessArticle An Investigation of the Reactions of Substituted Homoallylic Alcohols with Various Oxidation Reagents
Molecules 2002, 7(2), 104-111; doi:10.3390/70200104
Received: 19 June 2001 / Revised: 6 November 2001 / Accepted: 26 January 2002 / Published: 28 February 2002
Cited by 1 | PDF Full-text (98 KB) | HTML Full-text | XML Full-text
Abstract
Substituted homoallylic alcohols have been synthesised both by [2,3]-Wittig rearrangement of unsymmetrical bis-allylic ethers and reaction of alkenyl chloromethyl oxiranes with Mg/THF. These substrates were then oxidized using four different oxidants. When the substituted homoallylic alcohols were oxidized with pyridinium chlorochromate or [...] Read more.
Substituted homoallylic alcohols have been synthesised both by [2,3]-Wittig rearrangement of unsymmetrical bis-allylic ethers and reaction of alkenyl chloromethyl oxiranes with Mg/THF. These substrates were then oxidized using four different oxidants. When the substituted homoallylic alcohols were oxidized with pyridinium chlorochromate or zinc chlorochromate nonahydrate the corresponding carbonyl compounds were produced. The same substrates formed the corresponding allylic oxidation products together with epoxidation products when oxidized with t-BuOOH. When and t-BuOOH and catalytic amounts of OsO4 were used the allylic oxidation reaction was prevented and the only products formed were those in which the substituted double bond was epoxidized. Full article
Open AccessArticle Photooxygenation of Nimonol, a Tetranortriterpenoid from Azadirachta indica. A. Juss.
Molecules 2002, 7(2), 112-118; doi:10.3390/70200112
Received: 21 May 2001 / Revised: 19 December 2001 / Accepted: 21 December 2001 / Published: 28 February 2002
Cited by 7 | PDF Full-text (88 KB) | HTML Full-text | XML Full-text
Abstract
Nimonol (1), a tetranortriterpenoid isolated from the leaves of Azadirachta indica A. Juss (Meliaceae), upon photolysis undergoes both Diels-Alder and ene reactions with singlet oxygen at different sites leading to 14,15,20,21-diepoxy-23-nimonolactone (3), along with nimonolide (4), which have been well-characterised. The novelty [...] Read more.
Nimonol (1), a tetranortriterpenoid isolated from the leaves of Azadirachta indica A. Juss (Meliaceae), upon photolysis undergoes both Diels-Alder and ene reactions with singlet oxygen at different sites leading to 14,15,20,21-diepoxy-23-nimonolactone (3), along with nimonolide (4), which have been well-characterised. The novelty of the reported reactions lies in hitherto unreported formation of an α-epoxide in the ring D in tetranortriterpenoids. The photoproduct 4 exhibited antifeedancy comparable to that of azadirachtin-A, the most potent antifeedant constituent isolated from neem. Full article
Open AccessArticle Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones
Molecules 2002, 7(2), 119-123; doi:10.3390/70200119
Received: 7 May 2001 / Revised: 15 January 2002 / Accepted: 16 January 2002 / Published: 21 February 2002
Cited by 1 | PDF Full-text (26 KB)
Abstract
It has been shown that N-(3-oxoalkyl)chloroacetamides (1) can be converted into cis-3,4-epoxypiridin-2-ones (2) upon treatment with t-BuOK in a t-BuOH-C6H6 solution due to a resulting intramolecular Darzens reaction. It has been found that under kinetically controlled reaction conditions [...] Read more.
It has been shown that N-(3-oxoalkyl)chloroacetamides (1) can be converted into cis-3,4-epoxypiridin-2-ones (2) upon treatment with t-BuOK in a t-BuOH-C6H6 solution due to a resulting intramolecular Darzens reaction. It has been found that under kinetically controlled reaction conditions (NaOH/C6H6), besides the intramolecular Darzens reaction an intramolecular alkylation takes place. Full article
Open AccessArticle Synthesis of 5,6-Dihydropyridin-2(1H)-ones, 1,5,6,8,8a-Hexahydroisoquinolin-3(2H)-ones and 4a,5,6,7,8,8a-Hexahydroquinolin-2(1H)-ones by Intramolecular Wittig Reaction
Molecules 2002, 7(2), 124-128; doi:10.3390/70200124
Received: 7 May 2001 / Revised: 15 January 2002 / Accepted: 16 January 2002 / Published: 28 February 2002
Cited by 7 | PDF Full-text (35 KB) | HTML Full-text | XML Full-text
Abstract A new, universal and diastereospecific method has been developed for the synthesis of 5,6-dihydropyridin-2(1H)-ones, 1,5,6,8,8a-hexahydroisoquinolin-3(2H)-ones and 4a,5,6,7,8,8ahexahydroquinolin-2(1H)-ones (4) based on the intramolecular Wittig cyclization of the triphenyphosphonium salts 2 derived from the N-(3-oxoalkyl)–chloroacetamides 1. Full article
Open AccessArticle An Improved Three Step Synthesis of (-)-3β-Hydroxycarvone from (-)-Carvone
Molecules 2002, 7(2), 129-134; doi:10.3390/70200129
Received: 23 May 2001 / Revised: 15 January 2002 / Accepted: 31 January 2002 / Published: 28 February 2002
Cited by 2 | PDF Full-text (76 KB) | HTML Full-text | XML Full-text
Abstract
(-)-Carvone (3) has been efficiently transformed into (-)-3β-hydroxycarvone (1), which is expected to be a useful synthon or chiral template in the synthesis of natural molecules. This short and efficient synthesis of compound 1 involves regioselective and stereoselective α-hydroxylation of carvone via [...] Read more.
(-)-Carvone (3) has been efficiently transformed into (-)-3β-hydroxycarvone (1), which is expected to be a useful synthon or chiral template in the synthesis of natural molecules. This short and efficient synthesis of compound 1 involves regioselective and stereoselective α-hydroxylation of carvone via the trimethylsilyl-dienyl-ether derivative. Full article
Open AccessArticle Silica gel Catalyzed Synthesis of Quinophthalone Pigments Under Solvent-Free Conditions Using Microwave Irradiation
Molecules 2002, 7(2), 135-139; doi:10.3390/70200135
Received: 28 October 2001 / Revised: 28 January 2002 / Accepted: 1 February 2002 / Published: 28 February 2002
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Abstract Condensations of anhydrides and quinaldine derivatives are accelerated by microwave irradiation under solvent free conditions in the presence of silica gel as catalyst. Full article
Open AccessArticle Synthesis of Two Potentially Heptadentate (N4O3) Schiff-base Ligands Derived from Condensation of Tris(3-aminopropyl)-amine and Salicylaldehyde or 4-Hydroxysalicylaldehyde. Nickel(II) and Copper(II) Complexes of the Former Ligand
Molecules 2002, 7(2), 140-144; doi:10.3390/70200140
Received: 9 December 2001 / Revised: 6 February 2002 / Accepted: 11 February 2002 / Published: 28 February 2002
Cited by 20 | PDF Full-text (75 KB) | HTML Full-text | XML Full-text
Abstract
Two potentially heptadentate (N4O3) tripodal Schiff-base ligands: tris(3-(salicylideneimino)propyl)amine (H3L1) and tris(3-(4’-hydroxysalicylideneimino)-propyl)amine (H3L2) have been prepared and characterized by various spectroscopic methods (IR, FAB-MS, NMR). They are derived from the condensation reactions of tris(3-aminopropyl)amine (tpt), with 3 equivalents of [...] Read more.
Two potentially heptadentate (N4O3) tripodal Schiff-base ligands: tris(3-(salicylideneimino)propyl)amine (H3L1) and tris(3-(4’-hydroxysalicylideneimino)-propyl)amine (H3L2) have been prepared and characterized by various spectroscopic methods (IR, FAB-MS, NMR). They are derived from the condensation reactions of tris(3-aminopropyl)amine (tpt), with 3 equivalents of either salicylaldehyde or the ringsubstituted salicylaldehyde, 4-hydroxysalicylaldehyde. The nickel(II) and copper(II) complexes of H3L1 were obtained from the its reactions Ni(II) and Cu(II) salts in absolute methanol. These complexes were studied by IR and FAB-Mass spectrometry. Full article
Open AccessArticle Synthesis of Thieno[2,3-d]-1,3-dithiol-2-thiones from Thieno[2,3-d]-1,2,3-thiadiazoles: Matryoshka-type autoclave for high-temperature, high-pressure thermolysis microscale reactions
Molecules 2002, 7(2), 145-154; doi:10.3390/70200145
Received: 23 December 2001 / Accepted: 6 February 2002 / Published: 28 February 2002
PDF Full-text (157 KB) | HTML Full-text | XML Full-text
Abstract
Thieno[2,3-d]-1,2,3-thiadiazoles (1) react with carbon disulfide in a "Matryoshkatype" double compartment autoclave [1] to yield thieno[2,3-d]-1,3-dithiol-2-thiones (2). With BH3/Me2S the cyclic trithiocarbonate (2d) is cleaved and the product characterized after methylation as 4b. Compounds 7a and 7b are [...] Read more.
Thieno[2,3-d]-1,2,3-thiadiazoles (1) react with carbon disulfide in a "Matryoshkatype" double compartment autoclave [1] to yield thieno[2,3-d]-1,3-dithiol-2-thiones (2). With BH3/Me2S the cyclic trithiocarbonate (2d) is cleaved and the product characterized after methylation as 4b. Compounds 7a and 7b are prepared via the thieno[2,3-d]-1,3-dithiolium salts (6) followed by NaBH4-reduction. Full article
Open AccessArticle Functionalization of Phenyl Rings by Imidoylnitrenes. 3 The Effects of Resonance, Steric, and Inductive Properties on the Reactivity or Selectivity of Nitrenes and the Stability of their Precursors
Molecules 2002, 7(2), 189-199; doi:10.3390/70200189
Received: 12 November 2001 / Revised: 5 February 2002 / Accepted: 5 February 2002 / Published: 28 February 2002
Cited by 9 | PDF Full-text (69 KB) | HTML Full-text | XML Full-text
Abstract
The thermal decomposition of imidoyl azides (ArO-C=N-Z)-N3, (Ar = p-NO2-C6H4-, p-Br-C6H4-, p-Cl-C6H4-, p-C6H5-, p-CH3-C6H4-, 2,4-dimethyl-C6H3 [...] Read more.
The thermal decomposition of imidoyl azides (ArO-C=N-Z)-N3, (Ar = p-NO2-C6H4-, p-Br-C6H4-, p-Cl-C6H4-, p-C6H5-, p-CH3-C6H4-, 2,4-dimethyl-C6H3-, 2,4,6-trimethyl-C6H2-, p-CH3O-C6H4- and Z = p-CH3-C6H4-SO2-, 2,4,6-trimethyl-C6H2-SO2-,CN) in the solid phase and in anisole has been studied in detail. The sensitivity of nitrenes and nitrene precursors (imidoyl azides) towards substitution changes in the aryloxy (ArO) and Z moieties is examined. Full article
Open AccessArticle Synthesis of Substituted Phenyl N-(2-hydroxybenzyl)-N-Methylcarbamates
Molecules 2002, 7(2), 200-205; doi:10.3390/70200200
Received: 29 June 2001 / Revised: 29 January 2002 / Accepted: 30 January 2002 / Published: 28 February 2002
PDF Full-text (112 KB) | HTML Full-text | XML Full-text
Abstract Thirteen previously unreported substituted phenyl N-(2-hydroxybenzyl)-Nmethylcarbamates were prepared by the reaction of substituted 2-hydroxybenzyl-Nmethylamines with phenyl chlorocarbonates. They were identified by their 1H- and 13C-NMR spectra. Full article
Open AccessArticle marvin: A Platform for Chemoinformatics Software Development
Molecules 2002, 7(2), 206-238; doi:10.3390/70200206
Received: 11 October 2001 / Revised: 26 February 2002 / Accepted: 26 February 2002 / Published: 28 February 2002
PDF Full-text (239 KB) | HTML Full-text | XML Full-text
Abstract
A strategy for a new type of platform for chemoinformatics software development and its first implementation are presented. The basic task of such a platform is to apply sequences of computational methods to high numbers of molecules. The implementation presented is based [...] Read more.
A strategy for a new type of platform for chemoinformatics software development and its first implementation are presented. The basic task of such a platform is to apply sequences of computational methods to high numbers of molecules. The implementation presented is based on four major components: (a) the application manager, responsible for running programs and for data management; (b) executable applications that supply limited pieces of functionality; (c) syntax definitions for data and control files and (d) the runtime library which comprises routines for data handling and user interface. This simple concept is implemented in the software package marvin. Different computational methods are available within marvin, including parts of commercial software packages (e.g. molecular modeling, bioinformatics, statistics, etc.) as well as newly developed and innovative algorithms. The basic layout of marvin is described and a simple example illustrates its application. Full article
Open AccessArticle Synthesis of Some Aldoxime Derivatives of 4H-Pyran-4-ones
Molecules 2002, 7(2), 239-244; doi:10.3390/70200239
Received: 26 April 2001 / Revised: 26 December 2001 / Accepted: 15 February 2002 / Published: 28 February 2002
Cited by 1 | PDF Full-text (28 KB) | HTML Full-text | XML Full-text
Abstract Aldoxime derivatives of 4H-pyran-4-ones 4-7a,b have been synthesized by the reaction of di(aminoxymethyl) pyranones 3a,b with aromatic aldehydes. Full article
Open AccessArticle An Acylated Kaempferol Glycoside from Flowers of Foeniculum vulgare and F. Dulce
Molecules 2002, 7(2), 245-251; doi:10.3390/70200245
Received: 23 December 2001 / Revised: 16 February 2002 / Accepted: 23 February 2002 / Published: 28 February 2002
Cited by 16 | PDF Full-text (78 KB) | HTML Full-text | XML Full-text
Abstract
An acylated kaempferol glycoside, namely kaempferol-3-O-α-L-(2”,3”-di-E-pcoumaroyl)-rhamnoside (1) was isolated from the flowers of Foeniculum vulgare Mill. and F. dulce DC. It is thus isolated for the first time from family Apiaceae. In addition, the different organs of both plants afforded six flavonoid [...] Read more.
An acylated kaempferol glycoside, namely kaempferol-3-O-α-L-(2”,3”-di-E-pcoumaroyl)-rhamnoside (1) was isolated from the flowers of Foeniculum vulgare Mill. and F. dulce DC. It is thus isolated for the first time from family Apiaceae. In addition, the different organs of both plants afforded six flavonoid glycosides - namely afzelin (kaempferol-3-O-α-L-rhamnoside) (2), quercitrin (3), isorhamnetin-3-O-β-D-glucoside (4), isoquercitrin (5), rutin (6), and miquelianin (quercetin-3-O-β-D-glucuronide) (7). Structure elucidation of the above mentioned flavonoids was achieved by UV, 1H- and 13C-NMR, 1H-1H COSY, HMQC and EI-MS. Full article
Open AccessArticle Reactivity of 3-Ethoxycarbonyl Isoquinolinium Salts Towards Various Nucleophilic Reagents: Applications to the Synthesis of New 1,2-Dihydroisoquinoline-3-carboxylates
Molecules 2002, 7(2), 252-263; doi:10.3390/70200252
Received: 16 January 2002 / Revised: 19 February 2002 / Accepted: 20 February 2002 / Published: 28 February 2002
Cited by 5 | PDF Full-text (81 KB) | HTML Full-text | XML Full-text
Abstract Different types of novel 1,2-disubstituted 1,2-dihydro isoquinolines were synthesized by addition reactions of organolithium, alcoholates and borohydride reagents with various isoquinolinium salts. The leaving group character of the isoquinoline moiety was also evidenced. Full article
Open AccessArticle Mn (Br8TPPS) Supported on Amberlite IRA-400 as a Robust and Efficient Catalyst for Alkene Epoxidation and Alkane Hydroxylation
Molecules 2002, 7(2), 264-270; doi:10.3390/70200264
Received: 29 June 2001 / Revised: 17 February 2002 / Accepted: 18 February 2002 / Published: 28 February 2002
Cited by 25 | PDF Full-text (25 KB) | HTML Full-text | XML Full-text
Abstract Manganese (III) meso-tetrakis(p-sulfonatophenyl)-β-octabromoporphyrin supported on Amberlite IRA-400 [Mn(Br8TPPS)-Ad-400] is a robust and efficient catalyst for epoxidation of alkenes and hydroxylation of alkanes with sodium periodate at room temperature. Full article
Open AccessArticle Synthesis of 6-Methoxy-1-oxaspiro[4,5]deca-6,9-diene-8-one
Molecules 2002, 7(2), 315-319; doi:10.3390/70200315
Received: 23 January 2002 / Revised: 25 February 2002 / Accepted: 26 February 2002 / Published: 28 February 2002
Cited by 4 | PDF Full-text (26 KB) | HTML Full-text | XML Full-text
Abstract The synthesis of a new spirolactone is described. The title compound is obtained as a white solid in 46% yield from 3-(4-hydroxy-2-methoxyphenyl)propanoic acid using [Bis(trifluoroacetoxy)iodo]benzene (PIFA) as the oxidant. Full article

Review

Jump to: Research

Open AccessReview Synthesis and Reactions of Acenaphthenequinones-Part-2. The Reactions of Acenaphthenequinones
Molecules 2002, 7(2), 155-188; doi:10.3390/70200155
Received: 30 October 2001 / Revised: 11 February 2002 / Accepted: 11 February 2002 / Published: 28 February 2002
Cited by 6 | PDF Full-text (233 KB) | HTML Full-text | XML Full-text
Abstract The reactions of acenaphthenequinone and its derivatives with different nucleophiles, organic and inorganic reagents are reviewed. This survey also covers their oxidation and reduction reactions, in addition to many known reactions such as Friedel Crafts, Diels-Alder, bromination and thiolation. Full article
Open AccessReview Chemistry of the Genus Plectranthus
Molecules 2002, 7(2), 271-301; doi:10.3390/70200271
Received: 21 May 2001 / Revised: 11 September 2001 / Accepted: 15 February 2002 / Published: 28 February 2002
Cited by 39 | PDF Full-text (233 KB) | HTML Full-text | XML Full-text
Abstract
This review presents the phytochemical constituents of the genus Plectranthus reported up to 1999. Only a tetrameric derivative of caffeic acid was isolated from P. japonicus, but a group of long-chain alkylphenols, of possible taxonomic significance in the genus, was also isolated. [...] Read more.
This review presents the phytochemical constituents of the genus Plectranthus reported up to 1999. Only a tetrameric derivative of caffeic acid was isolated from P. japonicus, but a group of long-chain alkylphenols, of possible taxonomic significance in the genus, was also isolated. As a genus of the subfamily Nepetoideae, Plectranthus is free from iridoid glycosides and rich in essential oil (i.e. > 0.5% volatile oil on a dry weight basis). Diterpenoids are the more common secondary metabolites in Plectranthus. The majority of them are highly modified abietanoids. This seems to be similar to the pattern of diterpenoids observed for Salvia, but no clerodane diterpenoids were found in Plectranthus. Full article
Open AccessReview 1,3-Dipolar Cycloaddition Reactions of Substituted Benzyl Azides with Acetylenic Compounds
Molecules 2002, 7(2), 302-314; doi:10.3390/70200302
Received: 1 October 2001 / Revised: 10 December 2001 / Accepted: 14 December 2001 / Published: 28 February 2002
Cited by 14 | PDF Full-text (61 KB) | HTML Full-text | XML Full-text
Abstract
We review in this article some of our work which has been published over the last fifteen years in the area of 1,3-dipolar cycloaddition reactions of substituted benzyl azides with acetylenic compounds to form the corresponding 1,2-3-triazoles. Several triazole derivatives were transformed [...] Read more.
We review in this article some of our work which has been published over the last fifteen years in the area of 1,3-dipolar cycloaddition reactions of substituted benzyl azides with acetylenic compounds to form the corresponding 1,2-3-triazoles. Several triazole derivatives were transformed into triazolopyridazine and triazolo-1,3,4-oxadiazole derivatives upon their reactions with hydrazine. Full article

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