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Molecules, Volume 5, Issue 7 (July 2000), Pages 916-991, Articles M162-M171

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Research

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Open AccessArticle Novel Behavior of Thiiranium Radical Cation Intermediates. Reactions of Dimethyl Disulfide with Alkenes in the Presence of Pd(OAc)2
Molecules 2000, 5(7), 916-926; doi:10.3390/50700916
Received: 8 March 2000 / Revised: 7 June 2000 / Accepted: 20 June 2000 / Published: 7 July 2000
Cited by 1 | PDF Full-text (69 KB)
Abstract
Reaction of dimethyl disulfide (1) with cyclohexene (2a) in AcOH in the presence of Pd(OAc)2 yields trans-1-acetoxy-2-methylcyclohexane (3a). The equivalent reactions with hex-1-ene (2b) and 2-methylpent-1-ene (2c) or 1-methylcyclohex-1-ene (2d) preferentially give anti-Markovnikov and Markovnikov adducts 4 and 3, respectively,
[...] Read more.
Reaction of dimethyl disulfide (1) with cyclohexene (2a) in AcOH in the presence of Pd(OAc)2 yields trans-1-acetoxy-2-methylcyclohexane (3a). The equivalent reactions with hex-1-ene (2b) and 2-methylpent-1-ene (2c) or 1-methylcyclohex-1-ene (2d) preferentially give anti-Markovnikov and Markovnikov adducts 4 and 3, respectively, by acetoxymethylthiolation of the alkene. The Markovnikov regioselectivity 3b/4b for the reaction with 2b is higher than that for the reaction using AgOAc instead of Pd(OAc)2, which proceeds via a thiiranium ion. Addition of a polar solvent (MeCN or MeNO2) to the reactions with 2b or 2c using Pd(OAc)2 abnormally decreases the Markovnikov regioselectivity. The total yield of 3 and 4 increases with an increased concentration of AcOH. Compounds 3 and 4 are also formed and the reactions in MeCN or MeNO2 not containing AcOH. A solution of Pd(OAc)2 in 1 exhibits λmax 380 nm (log ε 3.6) assigned to the absorption of a relatively stable sulfonium salt. These indicate that the reactions using Pd(OAc)2 proceed by SN2 ringopening of a new type of thiiranium radical cations paired with −OAc via the sulfonium salts. The insensitivity of the 3/4 ratios to the reaction time at 25-60°C in the reactions with 2c-d shows the ring-opening to be controlled kinetically, but the increased ratio with reaction time at 116°C in the reaction with 2b suggests that the ring-opening is thermodynamically governed. The reaction product with 2d also undergoes a skeletal rearrangement to a thietanium radical cation to give 1-acetoxymethyl-2-methylthiocyclohexane. Full article
Open AccessArticle Benzamidomethylation with (Benzamidomethyl)triethylammonium Chloride. 2. A Simple Method for Benzamidomethylation of Thiols, Amines and Carboxylic Acids
Molecules 2000, 5(7), 927-936; doi:10.3390/50700927
Received: 27 March 2000 / Revised: 22 June 2000 / Accepted: 29 June 2000 / Published: 7 July 2000
Cited by 2 | PDF Full-text (42 KB)
Abstract
Thiols and amines were benzamidomethylated in water solution at room temperature with (benzamidomethyl)triethylammonium chloride (1) in the presence of a small quantity of triethylamine (pH>9). Benzamidomethyl thioethers (3a-d) and (benzamidomethyl) amines or di(benzamidomethyl)amines (5) were obtained in high yields (>90%) as well as
[...] Read more.
Thiols and amines were benzamidomethylated in water solution at room temperature with (benzamidomethyl)triethylammonium chloride (1) in the presence of a small quantity of triethylamine (pH>9). Benzamidomethyl thioethers (3a-d) and (benzamidomethyl) amines or di(benzamidomethyl)amines (5) were obtained in high yields (>90%) as well as S(CH2NHBz)2 in a reaction of 1 with Na2S. Benzamidomethyl esters RCOOCH2NHBz were obtained (60-75%) in reactions of carboxylic acids with 1 in chloroform or dioxane. Full article
Open AccessArticle Mass Spectra of Some 4- and 5-Substituted Derivatives of Benzoselenadiazoles
Molecules 2000, 5(7), 937-940; doi:10.3390/50700937
Received: 30 September 1999 / Accepted: 29 June 2000 / Published: 9 July 2000
Cited by 2 | PDF Full-text (18 KB)
Abstract Electron impact mass spectra of variety of eight 4-substituted and eight 5-substituted benzoselenadiazoles are presented and their spectral fragmentations are discussed. New mass spectra containing selenium in heterocyclic azole atom containing ring. Full article
Open AccessArticle Selective ipso-Nitration of tert-Butylcalix[4]arene Tripropylether
Molecules 2000, 5(7), 941-944; doi:10.3390/50700941
Received: 22 April 2000 / Accepted: 29 May 2000 / Published: 10 July 2000
Cited by 7 | PDF Full-text (22 KB)
Abstract An improved selective ipso-nitration of the tripropoxy derivative of tertbutylcalix[4]arene at the upper rim is described. The synthesized products are key intermediates for construction of molecular receptors based on calixarenes. Full article
Open AccessArticle Three-Dimensional Quantitative Structural Activity Relationship (3D-QSAR) Studies of Some 1,5-Diarylpyrazoles: Analogue Based Design of Selective Cyclooxygenase-2 Inhibitors
Molecules 2000, 5(7), 945-955; doi:10.3390/50700945
Received: 17 February 2000 / Revised: 26 June 2000 / Accepted: 26 June 2000 / Published: 8 July 2000
Cited by 14 | PDF Full-text (144 KB)
Abstract
Selective cyclooxygenase inhibitors have attracted much attention in recent times in the design of new non-steroidal anti-inflammatory drugs (NSAID). 3D-QSAR studies have been performed on a series of 1,5-diarylpyrazoles that act as selective cyclooxygenase-2 (COX-2) inhibitors, using three different methods: comparative molecular field
[...] Read more.
Selective cyclooxygenase inhibitors have attracted much attention in recent times in the design of new non-steroidal anti-inflammatory drugs (NSAID). 3D-QSAR studies have been performed on a series of 1,5-diarylpyrazoles that act as selective cyclooxygenase-2 (COX-2) inhibitors, using three different methods: comparative molecular field analysis (CoMFA) with partial least squares (PLS) fit; molecular field analysis (MFA) and; receptor surface analysis (RSA) with genetic function algorithms (GFA). The analyses were carried out on 30 analogues of which 25 were used in the training set and the rest considered for the test set. These studies produced reasonably good predictive models with high cross-validated and conventional r2 values in all the three cases. Full article
Open AccessArticle Spectral Characteristics of 2,7-Naphthyridines
Molecules 2000, 5(7), 956-960; doi:10.3390/50700956
Received: 27 March 2000 / Accepted: 22 June 2000 / Published: 27 June 2000
Cited by 1 | PDF Full-text (31 KB)
Abstract Substituent increments for the calculation of 1H- and 13C-NMR spectra and the MS characteristics of 2,7-naphthyridines substituted on one ring are presented. Full article
Open AccessArticle Photolytic Cleavage and Condensation Reactions of Cyclohexa-2,4-dienones with Diamines
Molecules 2000, 5(7), 961-966; doi:10.3390/50700961
Received: 29 April 2000 / Accepted: 29 June 2000 / Published: 23 July 2000
PDF Full-text (38 KB)
Abstract Cyclohexa-2,4-diene-1-one sulfone derivate undergoes ring cleavage to afford bis-amides containing a diene moiety on irradiation with visible light in the presence of various diamines. Full article
Open AccessArticle Reactions with Hydrazonoyl Halides. 31. Synthesis of Some New Pyrrolidino[3,4-c]pyrazolines, Pyrazoles, and Pyrazolo[3,4-d]pyridazines
Molecules 2000, 5(7), 967-973; doi:10.3390/50700967
Received: 29 May 2000 / Revised: 6 July 2000 / Accepted: 6 June 2000 / Published: 21 June 2000
Cited by 11 | PDF Full-text (50 KB)
Abstract Pyrrolidino[3,4-c]pyrazoline and pyrazole derivatives were synthesized via reactions of a substituted hydrazonoyl bromide with N-arylmaleimides and active methylene reagents, respectively. Synthesized pyrazoles were reacted with hydrazine hydrate to give the corresponding pyrazolo[3,4-d]pyridazines. Full article
Open AccessArticle Synthesis and Antifungal Activity of Musa Phytoalexins and Structural Analogs
Molecules 2000, 5(7), 974-980; doi:10.3390/50700974
Received: 18 January 2000 / Revised: 14 July 2000 / Accepted: 14 July 2000 / Published: 26 July 2000
Cited by 13 | PDF Full-text (33 KB)
Abstract Several perinaphthenone/phenylphenalenone compounds were synthesized to establish a relationship between structure and antifungal activity against Mycosphaerella fijiensis. Substitutions on the unsaturated carbonyl system or addition of a phenyl group reduced antibiotic activity. Full article

Other

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Open AccessShort Note N-(9-Fluorenylmethoxycarbonyl)-L-serine Amide
Molecules 2000, 5(7), M162; doi:10.3390/M162
Received: 10 April 2000 / Accepted: 25 April 2000 / Published: 10 July 2000
PDF Full-text (90 KB) | Supplementary Files
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note Cycloeucalen-3ß-(2-methyl Butanoate). New Cycloeucalen Isolated from the Espeletia barclayana Cuatr (Asteraceae)
Molecules 2000, 5(7), M163; doi:10.3390/M163
Received: 1 April 2000 / Accepted: 18 May 2000 / Published: 10 July 2000
PDF Full-text (119 KB) | Supplementary Files
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note 6-Amino-2-phenylimidazo[4,5-e][1,3]diazepine-4,8(1H, 5H)-dione
Molecules 2000, 5(7), M164; doi:10.3390/M164
Received: 17 May 2000 / Accepted: 2 June 2000 / Published: 10 July 2000
PDF Full-text (89 KB) | Supplementary Files
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note 1,2-Ethylene-bis(p-N2-phenylene-N1,N1-dimethylformamidine)
Molecules 2000, 5(7), M165; doi:10.3390/M165
Received: 16 May 2000 / Accepted: 2 June 2000 / Published: 10 July 2000
PDF Full-text (89 KB) | Supplementary Files
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note 1,2-Ethylene-bis(o-N2-phenylene-N1,N1-dimethylformamidine)
Molecules 2000, 5(7), M166; doi:10.3390/M166
Received: 16 May 2000 / Accepted: 2 June 2000 / Published: 10 July 2000
PDF Full-text (89 KB) | Supplementary Files
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note Bis[(2-benzylideneimino)phenyl]amine
Molecules 2000, 5(7), M167; doi:10.3390/M167
Received: 13 May 2000 / Accepted: 10 June 2000 / Published: 10 July 2000
PDF Full-text (18 KB) | Supplementary Files
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note 1-(2-Benzylaminophenyl)-2-phenylbenzimidazole
Molecules 2000, 5(7), M168; doi:10.3390/M168
Received: 13 May 2000 / Accepted: 10 June 2000 / Published: 10 July 2000
PDF Full-text (87 KB) | Supplementary Files
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note Trimethyl(trifluorovinyl)silane
Molecules 2000, 5(7), M169; doi:10.3390/M169
Received: 6 June 2000 / Accepted: 6 July 2000 / Published: 30 July 2000
PDF Full-text (84 KB) | Supplementary Files
Open AccessShort Note 5-(2-Thienylidene)barbituric Acid
Molecules 2000, 5(7), M170; doi:10.3390/M170
Received: 10 April 2000 / Accepted: 6 July 2000 / Published: 30 July 2000
PDF Full-text (86 KB) | Supplementary Files
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note 1-(4-Nitrophenyl)-1-octyne
Molecules 2000, 5(7), M171; doi:10.3390/M171
Received: 27 June 2000 / Accepted: 17 July 2000 / Published: 30 July 2000
Cited by 1 | PDF Full-text (83 KB) | Supplementary Files
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessNew Book Received Modern Carbonyl Chemistry. Edited by Junzo Otera
Molecules 2000, 5(7), 981-982; doi:10.3390/50700981
Received: 5 July 2000 / Published: 20 July 2000
PDF Full-text (13 KB)
Open AccessNew Book Received Applied Thin-Layer Chromatography. By Elke Hahn-Deinstrop
Molecules 2000, 5(7), 983-984; doi:10.3390/50700983
Received: 5 July 2000 / Published: 25 July 2000
PDF Full-text (12 KB)
Open AccessNew Book Received Classics in Hydrocarbon Chemistry. By Henning Hopf
Molecules 2000, 5(7), 985-986; doi:10.3390/50700985
Received: 5 July 2000 / Published: 25 July 2000
PDF Full-text (14 KB)
Open AccessNew Book Received Pharmacophore Perception, Development and Use in Drug Design. Edited by Osman F. Güner
Molecules 2000, 5(7), 987-989; doi:10.3390/50700987
Received: 5 July 2000 / Published: 26 July 2000
Cited by 4 | PDF Full-text (12 KB)
Open AccessNew Book Received Organic Synthesis on Solid Phase. By Florencio Zaragoza Dörwald
Molecules 2000, 5(7), 990-991; doi:10.3390/50700990
Received: 5 July 2000 / Published: 26 July 2000
PDF Full-text (12 KB)

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