Molecules

12 KiB

Open AccessBook 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 5125

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

Open AccessArticle

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 6159

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

Open AccessBook 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 5544

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

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Open AccessShort 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 3671

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

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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 3069

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

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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 2887

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

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(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 2934

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

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(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 2892

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

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(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 3005

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

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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 2960

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

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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 3135

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

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(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 3350

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

Open AccessArticle

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 10721

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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Figure 1

76 KiB

Open AccessArticle

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 6358

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

Open AccessArticle

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 6454

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

Open AccessArticle

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 10343

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

Open AccessArticle

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 7124

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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Figure 1

26 KiB

Open AccessArticle

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 6403

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

Open AccessArticle

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 239 | Viewed by 16395

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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Scheme 1

51 KiB

Open AccessArticle

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 9783

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

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Open AccessArticle

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 6652 | 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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Molecules, Volume 5, Issue 2 (February 2000) – 21 articles , Pages 99-199, Articles M134-M143

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