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Molecules, Volume 8, Issue 12 (December 2003), Pages 866-923

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Research

Open AccessArticle Synthesis and Crystal Structure of Hexakis(imidazole) nickel (II) O,O′-diphenyldithiophosphate [Ni(Im)6](Ph2O2PS2)2
Molecules 2003, 8(12), 866-872; doi:10.3390/81200866
Received: 10 October 2003 / Revised: 24 November 2003 / Accepted: 28 November 2003 / Published: 31 December 2003
Cited by 4 | PDF Full-text (310 KB) | HTML Full-text | XML Full-text
Abstract
The crystal and molecular structures of [Ni(Im)6](dtp)2 (Im = imidazole, dtp = O,O′-diphenyldithiophosphate) have been determined by X-ray crystallography. It crystallizes in the triclinic system, space group Pī, with cell parameters a = 9.375 (2), b = 12.324(3), c [...] Read more.
The crystal and molecular structures of [Ni(Im)6](dtp)2 (Im = imidazole, dtp = O,O′-diphenyldithiophosphate) have been determined by X-ray crystallography. It crystallizes in the triclinic system, space group Pī, with cell parameters a = 9.375 (2), b = 12.324(3), c = 13.285(3) Å, α = 107.86(3), β = 102.28(3), γ = 109.24(3), and Z = 1. The crystal structure of the title compound is built up of discrete monomeric molecules of [Ni(Im)6](dtp)2. The nickel (II) ion is hexacoordinated by six imidazole molecules and the coordination environment of Ni (II) is of octahedral geometry. In the solid state, a network of N-H···S intermolecular hydrogen bonds connect the Ni(Im)6 moieties and O,O′-diphenyldithiophosphate molecules, forming a three-dimensional structure. Full article
Open AccessArticle Silane Reduction of 5-Hydroxy-6-methyl-pyridine-3,4-dicarboxylic Acid Diethyl Ester: Synthesis of Vitamin B6
Molecules 2003, 8(12), 873-881; doi:10.3390/81200873
Received: 31 October 2003 / Revised: 1 December 2003 / Accepted: 10 December 2003 / Published: 31 December 2003
Cited by 4 | PDF Full-text (49 KB) | HTML Full-text | XML Full-text
Abstract
Alternative methods for the synthesis of pyridoxine have been investigated. The key intermediate, 5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid diethyl ester (5), was reduced with either a silane monomer (MeSiH(OEt)2) or a polysiloxane (polymethylhydrosiloxane, PMHS) to afford crude pyridoxine. An isolation technique utilizing a [...] Read more.
Alternative methods for the synthesis of pyridoxine have been investigated. The key intermediate, 5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid diethyl ester (5), was reduced with either a silane monomer (MeSiH(OEt)2) or a polysiloxane (polymethylhydrosiloxane, PMHS) to afford crude pyridoxine. An isolation technique utilizing a commercially available resin was devised, affording the desired product, vitamin B6, in an overall yield of 38-54 % and a purity of 76%. Full article
Open AccessArticle A Carboxylic Acid from Ilex integra
Molecules 2003, 8(12), 882-885; doi:10.3390/81200882
Received: 18 October 2003 / Revised: 18 December 2003 / Accepted: 18 December 2003 / Published: 31 December 2003
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Abstract (12E,14E,17E)-11-Hydroxy-12,14,17-dodecatrienoic acid was isolated from the stems of Ilex integra and its structure was determined on the basis of the spectroscopic data of its methyl ester. Full article
Open AccessArticle Epoxidation of Diosgenin, 25(R)-1,4,6-Spirostatrien-3-one and 25(R)-4,6-Spirostadien-3β-ol
Molecules 2003, 8(12), 886-893; doi:10.3390/81200886
Received: 18 September 2003 / Revised: 12 December 2003 / Accepted: 18 December 2003 / Published: 31 December 2003
Cited by 5 | PDF Full-text (156 KB) | HTML Full-text | XML Full-text
Abstract
Upon treatment of 25(R)-spirost-5-en-3β-ol (diosgenin), 25(R)-1,4,6-spirostatrien-3-one and 25(R)-4,6-spirostadien-3β-ol with 30% H2O2 and 5% NaOH in methanol, diosgenin did not react, 25(R)-1,4,6-spirostatrien-3-one was converted to 25(R)-1α,2α-epoxy-4,6-spirostadien-3-one and 25(R)-4,6-spirostadien-3β-ol was oxidized to give a small amount of 25(R)-4,6-spirostadien-3-one, while most of [...] Read more.
Upon treatment of 25(R)-spirost-5-en-3β-ol (diosgenin), 25(R)-1,4,6-spirostatrien-3-one and 25(R)-4,6-spirostadien-3β-ol with 30% H2O2 and 5% NaOH in methanol, diosgenin did not react, 25(R)-1,4,6-spirostatrien-3-one was converted to 25(R)-1α,2α-epoxy-4,6-spirostadien-3-one and 25(R)-4,6-spirostadien-3β-ol was oxidized to give a small amount of 25(R)-4,6-spirostadien-3-one, while most of the original starting material remained unchanged. On the other hand, reactions of diosgenin, 25(R)-1,4,6-spirostatrien-3-one and 25(R)-4,6-spirostadien-3β-ol with m-chloroperoxybenzoic acid in chloroform yielded 25(R)-5α,6α-epoxyspirostan-3β-ol, 25(R)-6α,7α-epoxy-1,4-spirostadien-3-one and 25(R)-4β,5β-epoxy-6-spirosten-3β-ol, respectively. Full article
Open AccessArticle Synthesis and Characterization of Benzo-15-Crown-5 Ethers with Appended N2O Schiff Bases
Molecules 2003, 8(12), 894-900; doi:10.3390/81200894
Received: 14 July 2003 / Revised: 30 October 2003 / Accepted: 3 November 2003 / Published: 31 December 2003
Cited by 37 | PDF Full-text (94 KB) | HTML Full-text | XML Full-text
Abstract
New derivatives of benzo-15-crown-5 with flexible appended N2O unsymmetrical Schiff bases were prepared by a two step procedure which involves: (i) preparation of N2O Schiff bases by condensation of hydrazine with salicylaldehyde, 3-methoxysalicylaldehyde or 2-hydroxy-1-naphtaldehyde and (ii) reaction [...] Read more.
New derivatives of benzo-15-crown-5 with flexible appended N2O unsymmetrical Schiff bases were prepared by a two step procedure which involves: (i) preparation of N2O Schiff bases by condensation of hydrazine with salicylaldehyde, 3-methoxysalicylaldehyde or 2-hydroxy-1-naphtaldehyde and (ii) reaction of the resulting NH2 functionalized compounds with 4’-formyl-benzo-15-crown-5. Full article
Open AccessArticle New Bioactive Azaartemisinin Derivatives
Molecules 2003, 8(12), 901-909; doi:10.3390/81200901
Received: 19 February 2003 / Revised: 5 October 2003 / Accepted: 24 November 2003 / Published: 31 December 2003
Cited by 3 | PDF Full-text (59 KB) | HTML Full-text | XML Full-text
Abstract
Reaction of artemisinin (1) with ethanolamine, followed by acid treatment produced the lactam (4S,8S,9S,13S,1R,5R,12R)-11-aza-11-(2-hydroxyethyl)-1,5,9-trimethyl-14,15-dioxatetracyclo [10.2.1.0<4,13>.0<8,13>]pentadecan-10-one (4) and the diol (1S,2S,6S,7S,5R,8R)-4-aza-5,6-dihydroxy-4-(2-hydroxyethyl)-2,8-dimethyl-7-(3-oxobutyl) bicyclo[4.4.0]decan-3-one (7). When ethylenediamine was used instead of the ethanolamine, the dimeric lactam (1S,4S,8S,9S,13S,5R,12R)-11-[2-((1S,4S,8S,9S,13S,5R,12R)-11-aza-1,5,9-trimethyl-14,15-dioxa-10-oxotetracyclo[10.2.1.0<4,13>.0<8,13>] pentadec-11-yl)ethyl]-11-aza-1,5,9-tri-methyl-14,15-dioxatetracyclo-[10.2.1.0<4,13>.0<8,13>]-pentadecan-10-one (8) was obtained. All compounds are new azaartemisinin derivatives lacking the peroxide functionality. These compounds were evaluated for antimalarial and cytotoxic activities. Only the dimer 8 was found to possess antimalarial activity, while only the diol 7 exhibited cytotoxic activity against human breast ductal carcinoma. Full article
Open AccessArticle 2-Arylhydrazonopropanals as Building Blocks in Heterocyclic Chemistry: Microwave Assisted Condensation of 2-Arylhydrazonopropanals with Amines and Active Methylene Reagents
Molecules 2003, 8(12), 910-923; doi:10.3390/81200910
Received: 25 July 2003 / Revised: 22 December 2003 / Accepted: 23 December 2003 / Published: 31 December 2003
Cited by 10 | PDF Full-text (161 KB) | HTML Full-text | XML Full-text
Abstract Utilization of 2-arylhydrazonopropanals for the synthesis of 2-arylhydrazonoimino propanones, 1,2,4-trizolo[4,3-a]pyrimidines, pyridopyridazine hydrazones, 3-oxaloalkanonitriles and 1,2,3-trizole derivatives by conventional heating and under microwave irradiation is described. Structural assignments are based on spectroscopic data and confirmed in some cases by X-ray crystallography. Full article

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