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Molecules, Volume 11, Issue 8 (August 2006), Pages 583-660

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Research

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Open AccessCommunication 1,4-Benzodiazepine N-Nitrosoamidines: Useful Intermediates in the Synthesis of Tricyclic Benzodiazepines
Molecules 2006, 11(8), 583-588; doi:10.3390/11080583
Received: 9 June 2006 / Revised: 31 July 2006 / Accepted: 1 August 2006 / Published: 9 August 2006
Cited by 8 | PDF Full-text (43 KB) | HTML Full-text | XML Full-text
Abstract
1,4-Benzodiazepine N-nitrosoamidines have been used as scaffolds for the preparation of different tricyclic derivatives. Replacement of the N-nitrosoamidine moiety through treatment with the nucleophiles acetylhydrazine, aminoacetaldehyde dimethylacetal and 1-amino-2-propanol, followed by an acid-catalyzed cyclization step, afforded triazolo and imidazobenzodiazepines 1, 6, and 7,
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1,4-Benzodiazepine N-nitrosoamidines have been used as scaffolds for the preparation of different tricyclic derivatives. Replacement of the N-nitrosoamidine moiety through treatment with the nucleophiles acetylhydrazine, aminoacetaldehyde dimethylacetal and 1-amino-2-propanol, followed by an acid-catalyzed cyclization step, afforded triazolo and imidazobenzodiazepines 1, 6, and 7, respectively, in good yields. When acetylhydrazine is used as a nucleophile, the overall process provides an alternative route to alprazolam (1b) and triazolam (1c), respectively. Full article
Open AccessArticle Synthesis and Molecular Structures of Two [1,4-bis(3-pyridyl)-2,3-diazo-1,3-butadiene]-dichloro-Zn(II) Coordination Polymers
Molecules 2006, 11(8), 589-596; doi:10.3390/11080589
Received: 5 June 2006 / Revised: 30 July 2006 / Accepted: 31 July 2006 / Published: 10 August 2006
Cited by 4 | PDF Full-text (265 KB) | HTML Full-text | XML Full-text
Abstract
Two novel coordination polymers with 3D metal-organic frameworks (MOFs) have been synthesized by reacting 1,4-bis(3-pyridyl)-2,3-diazo-1,3-butadiene (L) with zinc dichloride. Both compounds have the same repeating unit consisting of a distorted tetrahedral Zn(II) center coordinated by two chlorides and two pyridyl nitrogen atoms of
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Two novel coordination polymers with 3D metal-organic frameworks (MOFs) have been synthesized by reacting 1,4-bis(3-pyridyl)-2,3-diazo-1,3-butadiene (L) with zinc dichloride. Both compounds have the same repeating unit consisting of a distorted tetrahedral Zn(II) center coordinated by two chlorides and two pyridyl nitrogen atoms of two bridging bismonodentate L ligands, however, different structural conformations have been found, one forming a helical chain and the other producing a square-wave chain. The intermolecular C−H···Cl hydrogen bonds in 1 and 2 play important roles in the formation of three-dimensional coordination polymers. Compound 1 crystallized in an orthorhombic space group Pna21 with a = 7.9652(3), b = 21.4716(7), c = 8.2491(3)Å, V = 1410.81(9) Å 3 and Z = 4. Compound 2 crystallized in a monoclinic space group P21/n with a = 9.1752(3), b = 14.5976(4), c = 10.3666(3) Å , β = 98.231(2)°, V = 1374.16(7) Å 3 and Z = 4. Full article
Open AccessCommunication One-Pot Synthesis of 5-Arylidene-2-Imino-4-Thiazolidinones under Microwave Irradiation
Molecules 2006, 11(8), 597-602; doi:10.3390/11080597
Received: 2 June 2006 / Revised: 24 July 2006 / Accepted: 25 July 2006 / Published: 10 August 2006
Cited by 26 | PDF Full-text (48 KB) | HTML Full-text | XML Full-text
Abstract A rapid and easy solvent free one-pot synthesis of 5-arylidene-2-imino-4- thiazolidinones by condensation of the thioureas with chloroacetic acid and an aldehyde under microwave-irradiation is described. Full article
Open AccessArticle Epibatidine Alkaloid Chemistry: 5. Domino-Heck Reactions of Azabicyclic and Tricyclic Systems
Molecules 2006, 11(8), 603-614; doi:10.3390/11080603
Received: 26 July 2006 / Revised: 11 August 2006 / Accepted: 12 August 2006 / Published: 16 August 2006
Cited by 25 | PDF Full-text (77 KB) | HTML Full-text | XML Full-text
Abstract Palladium-catalyzed hydroarylations and additional domino reactions of aza- bicyclic and tricyclic norbornene derivatives were investigated and a series of new epibatidine analogues were synthesized. Full article
Open AccessArticle Synthesis of Conformationally Constrained Aryl- or Heteroarylpiperazinyl Derivatives of Selected Imides as 5-HT1A Receptor Ligands
Molecules 2006, 11(8), 615-626; doi:10.3390/11080615
Received: 14 June 2006 / Revised: 3 August 2006 / Accepted: 11 August 2006 / Published: 23 August 2006
Cited by 5 | PDF Full-text (90 KB) | HTML Full-text | XML Full-text
Abstract The preparation of a number of cyclic imide 5-HT1A receptor ligandderivatives has been described. Their structures were conformationally constrained byintroducing rigid linkers containing unsaturated bonds or aromatic benzene rings. Thesecompounds are expected to possess anxiolytic and antidepressant activity. Full article
Open AccessArticle Formal Synthesis of the ACE Inhibitor Benazepril·HCl via an Asymmetric Aza-Michael Reaction
Molecules 2006, 11(8), 641-648; doi:10.3390/11080641
Received: 26 June 2006 / Revised: 20 July 2006 / Accepted: 23 August 2006 / Published: 23 August 2006
Cited by 6 | PDF Full-text (100 KB) | HTML Full-text | XML Full-text
Abstract
A formal enantioselective synthesis of benazepril·HCl (4), an anti- hypertensive drug, is reported. Our synthesis employed an asymmetric aza-Michael addition of L-homophenylalanine ethyl ester (LHPE, 1) to 4-(2-nitrophenyl)-4-oxo- but-2-enoic acid methyl ester (6) as the key step to prepare (2S,3’S)-2-(2-oxo-2,3,4,5- tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl
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A formal enantioselective synthesis of benazepril·HCl (4), an anti- hypertensive drug, is reported. Our synthesis employed an asymmetric aza-Michael addition of L-homophenylalanine ethyl ester (LHPE, 1) to 4-(2-nitrophenyl)-4-oxo- but-2-enoic acid methyl ester (6) as the key step to prepare (2S,3’S)-2-(2-oxo-2,3,4,5- tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester (8), which is the key intermediate leading to benazepril·HCl (4). Full article
Open AccessArticle Efficient Ce(NO3)3·6H2O-Catalyzed Solvent-Free Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones
Molecules 2006, 11(8), 649-654; doi:10.3390/11080649
Received: 27 October 2005 / Revised: 9 May 2006 / Accepted: 23 August 2006 / Published: 23 August 2006
Cited by 30 | PDF Full-text (57 KB) | HTML Full-text | XML Full-text
Abstract Cerium(III) nitrate hexahydrate efficiently catalyzes the three-component Biginelli reaction under solvent-free conditions of an aldehyde, a β-keto ester or β- diketone and urea or thiourea to afford the corresponding 3,4-dihydropyrimidin-2(1H)- ones or –thiones in excellent yields. Full article
Open AccessArticle Application of the Solid-Phase Julia–Lythgoe Olefination in Vitamin D Side-Chain Construction
Molecules 2006, 11(8), 655-660; doi:10.3390/11080655
Received: 11 August 2006 / Accepted: 22 August 2006 / Published: 26 August 2006
Cited by 4 | PDF Full-text (64 KB) | HTML Full-text | XML Full-text
Abstract An example of the Julia–Lythgoe attachment of the vitamin D side chain to a solid-phase linked Inhoffen–Lythgoe diol derived CD-ring fragment is reported. Full article

Review

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Open AccessReview Development of Fluorous Lewis Acid-Catalyzed Reactions
Molecules 2006, 11(8), 627-640; doi:10.3390/11080627
Received: 5 July 2006 / Revised: 26 July 2006 / Accepted: 26 July 2006 / Published: 23 August 2006
Cited by 11 | PDF Full-text (326 KB) | HTML Full-text | XML Full-text
Abstract
Organic synthetic methodology in the 21st century aims to conform to the principles of green sustainable chemistry (GSC) and we may expect that in the future, the realization of GSC will be an important objective for chemical industries. An important aim of synthetic
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Organic synthetic methodology in the 21st century aims to conform to the principles of green sustainable chemistry (GSC) and we may expect that in the future, the realization of GSC will be an important objective for chemical industries. An important aim of synthetic organic chemistry is to implement waste-free and environmentally-benign industrial processes using Lewis acids as versatile as aluminum choride. A key technological objective of our work in this area has been to achieve a “catalyst recycling system that utilizes the high activity and structural features of fluorous Lewis acid catalysts”. Thus, we have developed a series of novel fluorous Lewis acid catalysts, namely the ytterbium(III), scandium(III), tin(IV) or hafnium(IV) bis(perfluoroalkanesulfonyl)amides or tris(perfluoro- alkanesulfonyl)methides. Our catalysts are recyclable and effective for acylations of alcohols and aromatics, Baeyer-Villiger reactions, direct esterifications and transesterifications in a fluorous biphasic system (FBS), in supercritical carbon dioxide and on fluorous silica gel supports. Full article

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