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Molecules, Volume 5, Issue 2 (February 2000) – 21 articles , Pages 99-199, Articles M134-M143

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12 KiB  
Book Review
Templated Organic Synthesis. Edited by F. Diederich ([email protected]) and Peter J. Stang ([email protected]). Wiley-VCH: Weinheim. 1999. XX+411 pp. 268 DM. ISBN 3-527-29666-2
by Shu-Kun Lin
Molecules 2000, 5(2), 195-197; https://doi.org/10.3390/50200195 - 25 Feb 2000
Viewed by 5004
Abstract
Physicochemical theoretical development has been dwarfed by the abundant experimental achievements in molecular recognition studies, including the template effects reported in this book [1-3].[...] Full article
36 KiB  
Article
Synthesis of N-(2-Cyanophenyl)chloromethanimidoyl Chloride
by Pavel Pazdera, Hana Divišová, Helena Havlišová and Petr Borek
Molecules 2000, 5(2), 189-194; https://doi.org/10.3390/50200189 - 24 Feb 2000
Cited by 29 | Viewed by 6003
Abstract
N-(2-Cyanophenyl)chloromethanimidoyl chloride (3) was prepared from 2-isothiocyanatobenzonitrile by the reaction with sulfuryl chloride or gaseous chlorine in an inert solvent. It was found that N-(2-cyanophenyl)chloromethanimidothioic chloride (2) and bis[N-(cyanophenyl)chloromethanimidoyl] sulfide (7) are intermediates of this reaction. The chloride 3 was obtained also by [...] Read more.
N-(2-Cyanophenyl)chloromethanimidoyl chloride (3) was prepared from 2-isothiocyanatobenzonitrile by the reaction with sulfuryl chloride or gaseous chlorine in an inert solvent. It was found that N-(2-cyanophenyl)chloromethanimidothioic chloride (2) and bis[N-(cyanophenyl)chloromethanimidoyl] sulfide (7) are intermediates of this reaction. The chloride 3 was obtained also by a three-component one-pot reaction of N-(2-cyanophenyl)-formamide in the present of thionyl chloride and sulfuryl chloride. (2-Cyanophenyl)-(1-{[(2-cyanophenyl)-imino]methoxy}methylidene)ammonium chloride (6) was detected as a by-product of this reaction. Identity of all reaction products was confirmed by GC-MS, FTIR, 1H and 13C NMR spectroscopy. Full article
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Scheme 1

8 KiB  
Book Review
Combinatorial Chemistry. Synthesis, Analysis, Screening. Edited by Günther Jung ([email protected]). Wiley-VCH: Weinheim. 1999. XXXII+602 pp. 268 DM. ISBN 3-527-29869-X
by Shu-Kun Lin
Molecules 2000, 5(2), 198-199; https://doi.org/10.3390/50200198 - 23 Feb 2000
Viewed by 5389
Abstract
This is not only a book written by specialists for specialists, but also for everyone who wants to brush up on their knowledge on the rapidly and ever-growing field of combinatorial chemistry.[...] Full article
22 KiB  
Short Note
Ethyl 2-(n-Butylamino)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate
by Lajos Kovács and Péter Forgó
Molecules 2000, 5(2), M143; https://doi.org/10.3390/M143 - 23 Feb 2000
Cited by 2 | Viewed by 3502
Abstract
Ethyl 2-cyano-3,3-bis(methylthio)acrylate 1 [1] (3.255 g; 15.0 mmol) was dissolved in anhydrous ethanol (100 mL), n-butylamine (1.100 g; 15.0 mmol) was added and the solution was heated to reflux for 2 h in a flask equipped with a gas outlet to remove the [...] Read more.
Ethyl 2-cyano-3,3-bis(methylthio)acrylate 1 [1] (3.255 g; 15.0 mmol) was dissolved in anhydrous ethanol (100 mL), n-butylamine (1.100 g; 15.0 mmol) was added and the solution was heated to reflux for 2 h in a flask equipped with a gas outlet to remove the evolving methanethiol (hood).[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
91 KiB  
Short Note
4-(5-Methyl-2-furfuryl)iden-2-furfurylaminobutanolide
by Lyudmila N. Sorotskaya, Tat'yana Ya. Kaklyugina and Larisa A. Badovskaya
Molecules 2000, 5(2), M142; https://doi.org/10.3390/M142 - 23 Feb 2000
Viewed by 2926
Abstract
4-(5-Methyl-2-furfuryl)iden-2-furfurylaminobutanolide was prepared by the reaction of 4-(5-methyl- 2-furfuryl)iden-2-butenolide and furfurylamine according to a literature procedure [1].[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
89 KiB  
Short Note
3-Benzyl-4-(N-benzylcarbamoylmethyl)-2-(3-pyridyl)-1,3-oxazolidine
by Marina A. Tlekhusezh, Roman V. Makuilov and Larisa A. Badovskaya
Molecules 2000, 5(2), M141; https://doi.org/10.3390/M141 - 23 Feb 2000
Cited by 1 | Viewed by 2739
Abstract
The title compound was synthesized by the reaction of N-benzyl-3-benzylamino-4-hydroxybutanamide with 3-pyridinecarboxaldehyde using the procedure described in [1].[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
97 KiB  
Short Note
(4R)-1'-Acetyl-2,3-O-isopropylidene-methylspiro [4,6-dideoxy-ß-D-ribo-hexopyranosid-4,5'-imidazolidin]-2',4'-dione
by Bohumil Steiner, Jan Gajdos and Miroslav Koos
Molecules 2000, 5(2), M140; https://doi.org/10.3390/M140 - 23 Feb 2000
Cited by 2 | Viewed by 2809
Abstract
Acetylation of hydantoins (imidazolidin-2,4-diones) and their 5-substituted derivatives normally occurs more readily in the 1-position [1].[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
94 KiB  
Short Note
(4R,2'R,3'R,5'R)-3-[3,5-Bis(tert-butyldimethylsilyloxy)-1-oxo-2-(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone
by Margaret A. Brimble and Josephine S. O. Park
Molecules 2000, 5(2), M138; https://doi.org/10.3390/M138 - 23 Feb 2000
Viewed by 2781
Abstract
To a solution of alcohol 1 (225 mg, 0.43 mmol) [1] in dry N,N-dimethylformamide (0.9 ml) at 0°C under an atmosphere of nitrogen was added imidazole (72 mg, 1.1 mmol) and tert-butyldimethylsilyl chloride (67 mg, 0.45 mmol). Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
92 KiB  
Short Note
(4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-1-oxo-2,3-bis(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone
by Margaret A. Brimble and Josephine S. O. Park
Molecules 2000, 5(2), M137; https://doi.org/10.3390/M137 - 23 Feb 2000
Viewed by 2864
Abstract
To a suspension of sodium hydride (5.9 mg, 60% in oil, 0.15 mmol) in tetrahydrofuran (0.34 ml) which contained a few drops of N,N-dimethylformamide, under nitrogen at 0°C, was added alcohol 1 (65 mg, 0.11 mmol) [1] in tetrahydrofuran (1.7 ml).[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
93 KiB  
Short Note
3-[5-(tert-Butyldimethylsilyloxy)-3-(3,5-dinitrobenzoyl)-1-oxo- 2-(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone
by Margaret A. Brimble and Josephine S. O. Park
Molecules 2000, 5(2), M136; https://doi.org/10.3390/M136 - 23 Feb 2000
Viewed by 2801
Abstract
A mixture of alcohol 1 (104 mg, 0.20 mmol) [1], triethylamine (41 l, 0.30 mmol) and 3,5-dinitrobenzoyl chloride (55 mg, 0.24 mmol) in dichloromethane (2 ml) was stirred for 2 h. at 30ºC.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
93 KiB  
Short Note
3-[5-(tert-Butyldimethylsilyloxy)-3-p-nitrobenzoyl-1-oxo- 2-(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone
by Margaret A. Brimble and Josephine S. O. Park
Molecules 2000, 5(2), M135; https://doi.org/10.3390/M135 - 23 Feb 2000
Viewed by 2952
Abstract
A mixture of alcohol 1 (121 mg, 0.23 mmol) [1], triethylamine (48 l, 0.34 mmol) and p-nitrobenzoyl chloride (51 mg, 0.28 mmol) in dichloromethane (2 ml) was stirred for 2 h. at 30ºC.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
93 KiB  
Short Note
(6bR*,9aR*)-6-(2-Benzyloxy-1-oxoethyl)-6b,9a-dihydro-5-hydroxy- 4-methoxyfuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one
by Margaret A. Brimble and Josephine S. O. Park
Molecules 2000, 5(2), M134; https://doi.org/10.3390/M134 - 23 Feb 2000
Viewed by 3208
Abstract
A solution of ceric ammonium nitrate (37 mg, 0.067 mmol) in water was added dropwise to a vigorously stirred solution of naphthol 1 (13 mg, 0.036 mmol) [1] in acetonitrile (2.2 ml) at room temperature and stirred for 15 min.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
72 KiB  
Article
Synthesis of the Formal Diels-Alder Adducts of N-substituted Dehydromaleimides and Anthracene
by Mario Smet, David Corens, Luc Van Meervelt and Wim Dehaen
Molecules 2000, 5(2), 179-188; https://doi.org/10.3390/50200179 - 21 Feb 2000
Cited by 18 | Viewed by 10493
Abstract
A new class of roof-shaped dibenzobarrelenemaleimide derivatives was prepared by the condensation of a bridged maleic anhydride with amines. A para-substituted bifunctional derivative was proven to be a 1:2 complex with acetone by an X-ray crystallographic study. Full article
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76 KiB  
Article
Effect of Microwave Irradiation on the Condensation of 6-Substituted 3-Formylchromones with Some Five-membered Heterocyclic Compounds
by Margita Lacova, Renata Gasparova, Dusan Loos, Tibor Liptay and Nada Pronayova
Molecules 2000, 5(2), 167-178; https://doi.org/10.3390/50200167 - 19 Feb 2000
Cited by 39 | Viewed by 6174
Abstract
Different types of 3-substituted 4H-4-oxobenzopyrans were prepared by microwave irradiation as well as by a classical method. The beneficial effect of microwave irradiation on the aldol condensation of 3-formylchromones with 2-imino-1-methylimidazolidine-4-one (creatinine), 2-thioxoimidazolidine-4-one (thiohydantoin) and 2-ethyl-2-thioxothiazolidin-4-one (3-ethylrhodanine) in different reaction media [...] Read more.
Different types of 3-substituted 4H-4-oxobenzopyrans were prepared by microwave irradiation as well as by a classical method. The beneficial effect of microwave irradiation on the aldol condensation of 3-formylchromones with 2-imino-1-methylimidazolidine-4-one (creatinine), 2-thioxoimidazolidine-4-one (thiohydantoin) and 2-ethyl-2-thioxothiazolidin-4-one (3-ethylrhodanine) in different reaction media is described. Our results show that the effect of microwave irradiation on the reactions studied was a shortening of the reaction times and a smooth increase in the yields. The subsequent reactions of the product with some nucleophiles are discussed. The structure of the products was proven by elemental analysis, IR and NMR spectra. Full article
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Scheme 1

34 KiB  
Article
Diels-Alder Cycloaddition of Cyclopentadiene to a Bis-naphthoquinone
by Margaret A. Brimble and Letecia J. Duncalf
Molecules 2000, 5(2), 162-166; https://doi.org/10.3390/50200162 - 19 Feb 2000
Cited by 6 | Viewed by 6279
Abstract
Addition of cyclopentadiene to bis-naphthoquinone (1) afforded predominantly the endo-endo [4+2] cycloadduct (2). Full article
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Scheme 1

51 KiB  
Article
Synthesis of 4-O-Methylcedrusin. Selective Protection of Catechols with Diphenyl Carbonate
by Stefaan M. O. Van Dyck, Guy L. F. Lemière, Tim H. M. Jonckers and Roger Dommisse
Molecules 2000, 5(2), 153-161; https://doi.org/10.3390/50200153 - 18 Feb 2000
Cited by 23 | Viewed by 10052
Abstract
4-O-Methylcedrusin, a minor component in ‘sangre de drago’, has been synthesized using a strategy of successive protection and deprotection reactions under very mild conditions. The key step of this synthesis is a selective protection of a catechol group as a cyclic carbonate in [...] Read more.
4-O-Methylcedrusin, a minor component in ‘sangre de drago’, has been synthesized using a strategy of successive protection and deprotection reactions under very mild conditions. The key step of this synthesis is a selective protection of a catechol group as a cyclic carbonate in the presence of an isolated phenol group. Full article
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Scheme 1

369 KiB  
Article
1,3-Dipolar Cycloadditions of N-Benzyl Furfuryl Nitrones with Electron-rich Alkenes
by Pedro Merino, Sonia Anoro, Francisco L. Merchan and Tomas Tejero
Molecules 2000, 5(2), 132-152; https://doi.org/10.3390/50200132 - 18 Feb 2000
Cited by 9 | Viewed by 6978
Abstract
The 1,3-dipolar cycloaddition reaction of N-benzyl-C-(2-furyl)nitrones with electron-rich alkenes gives preferentially trans-substituted 3,5-disubstituted isoxazolidines (endo approach). These experimental results are in good qualitative agreement with the predicted ones by semiempirical (AM1 and PM3) and ab initio (HF/3-21G) methods. Full article
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26 KiB  
Article
Unexpected Thorpe Reaction of an α-Alkoxynitrile
by Lajos Kovács
Molecules 2000, 5(2), 127-131; https://doi.org/10.3390/50200127 - 17 Feb 2000
Cited by 4 | Viewed by 6240
Abstract
α-Alkoxynitrile 1 in the presence of tris(methylthio)methyllithium 2 at –78ºC gave the dimer 5 instead of the expected C1-elongated product 3. The formation of compound 5 is explained in terms of anion formation and self-condensation, a variant of the Thorpe reaction. [...] Read more.
α-Alkoxynitrile 1 in the presence of tris(methylthio)methyllithium 2 at –78ºC gave the dimer 5 instead of the expected C1-elongated product 3. The formation of compound 5 is explained in terms of anion formation and self-condensation, a variant of the Thorpe reaction. Scrutinizing the 1H NMR spectra revealed that the enamine tautomer 5b is predominant over the imine 5a in the solvents investigated. Full article
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Scheme 1

101 KiB  
Article
Novel Coumarin Derivatives with Expected Biological Activity
by Z. M. Nofal, M. I. El-Zahar and S. S. Abd El-Karim
Molecules 2000, 5(2), 99-113; https://doi.org/10.3390/50200099 - 16 Feb 2000
Cited by 235 | Viewed by 16027
Abstract
A number of novel 3-bromo-4-methyl-7-methoxy-8-amino substituted coumarins and 2-substituted 7-bromo-6-methyl-8H-pyrano-benzimidazoles, benzoxazoles and/or benzoxazine-8-ones were synthesized for the purpose of pharmacological evaluation. Some representative compounds showed antitumor activity in vitro on Ehrlich ascites carcinoma in the preliminary testing. Full article
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51 KiB  
Article
NaY Zeolite: A Useful Catalyst for Nitrile Hydrolysis
by Dragana R. Milić, Dejan M. Opsenica, Borivoje Adnađević and Bogdan A. Šolaja
Molecules 2000, 5(2), 118-126; https://doi.org/10.3390/50200118 - 12 Feb 2000
Cited by 23 | Viewed by 9570
Abstract
The NaY zeolite catalysed hydrolysis of nitriles to primary amides is reported. It is found that aryl nitriles with strong electron-withdrawing substituents and cyanopyridines are readily hydrolysed in the water suspension, while aliphatic nitriles do not react. Full article
30 KiB  
Article
An Improved Synthesis of 3b-Acetoxy-lanost-8-en-24-one (24-Ketolanosteryl Acetate)
by Edward J. Parish, Hang Sun, Stephen Kizito and Terrence L. Boos
Molecules 2000, 5(2), 114-117; https://doi.org/10.3390/50200114 - 11 Feb 2000
Cited by 5 | Viewed by 6466 | Retraction
Abstract
The oxidation of a borane intermediate by PFC provides a convenient synthesis of 24-ketolanosteryl acetate. Full article
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Scheme 1

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