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Molecules, Volume 5, Issue 10 (October 2000) – 12 articles , Pages 1080-1181

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Open AccessArticle
Regioselective Oxidation of 3-Substituted Pyridinium Salts
Molecules 2000, 5(10), 1175-1181; https://doi.org/10.3390/51001175 - 31 Oct 2000
Cited by 3 | Viewed by 5811
Abstract
(1'R)-(+)-3-Hydroxymethyl-1-(1'-phenyl-ethyl)-pyridinium chloride (1), 1-benzyl-3-[1', 3']-dioxolan-2'-yl-pyridinium chloride (2) and (2'S, 4'S, 5'R)-(-)-1-benzyl-3-(3',4'-dimethyl-5'-phenyl-oxazolidin-2'-yl)-pyridinium bromide (3), were transformed by oxidation with potassium ferricyanide into the corresponding 1H-pyridin-2-ones in excellent yields with high regioselectivity. Full article
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Open AccessArticle
One-pot Syntheses of Fused Quinazolines by Reaction of N-(2-Cyanophenyl)chloromethanimidoyl Chloride. I. A New Synthesis of 1,3-Oxazolo- and 1,3-Oxazino[2,3-b]quinazolines
Molecules 2000, 5(10), 1166-1174; https://doi.org/10.3390/51001166 - 31 Oct 2000
Cited by 26 | Viewed by 4633
Abstract
12H-Benzo[1,3]oxazolo[2,3-b]quinazolin-12-imine (5a), 9-chloro-12Hbenzo[1,3]oxazolo[2,3-b]quinazolin-12-imine (5b), 2,3-dihydro-5H-[1,3]oxazolo[2,3-b]quinazolin-5-imine (5c), 2,3-dihydro-3,3-dimethyl-5H-[1,3]oxazolo[2,3-b]quinazolin-5-imine (5d) and 3,4--dihydro-2H,6H-[1,3]oxazino[2,3-b]quinazolin-6-imine (5e) were synthesized in a one-pot reaction of N-(2-cyanophenyl)chloromethanimidoyl chloride (1) with 2-aminophenols, 2-aminoethanol, and 3-aminopropanol in the presence of [...] Read more.
12H-Benzo[1,3]oxazolo[2,3-b]quinazolin-12-imine (5a), 9-chloro-12Hbenzo[1,3]oxazolo[2,3-b]quinazolin-12-imine (5b), 2,3-dihydro-5H-[1,3]oxazolo[2,3-b]quinazolin-5-imine (5c), 2,3-dihydro-3,3-dimethyl-5H-[1,3]oxazolo[2,3-b]quinazolin-5-imine (5d) and 3,4--dihydro-2H,6H-[1,3]oxazino[2,3-b]quinazolin-6-imine (5e) were synthesized in a one-pot reaction of N-(2-cyanophenyl)chloromethanimidoyl chloride (1) with 2-aminophenols, 2-aminoethanol, and 3-aminopropanol in the presence of a base. The course of the reaction was controlled by the temperature and the amount of base used. N-(2-Cyanophenyl)-(2-hydroxyanilino)methanimidoyl chloride (3a), 2-chloro-3-(2-hydroxyphenyl)-3,4-dihydroquinazolin-4-imine (4a) and 6-imino-2H, 3H, 4H, 6H, 11H-1,3-oxazino[2,3-b]-5-quinazolinium chloride (6) were identified as intermediates of the one-pot process. Full article
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Open AccessArticle
A New Pathway to 3-Hetaryl-2-oxo-2H-chromenes: On the Proposed Mechanisms for the Reaction of 3-Carbamoyl-2-iminochromenes with Dinucleophiles
Molecules 2000, 5(10), 1146-1165; https://doi.org/10.3390/51001146 - 31 Oct 2000
Cited by 35 | Viewed by 5665
Abstract
The present account summarizes the author's studies to elucidate the mechanisms of the recently reported rearrangements resulting from inter- and/or intramolecular reactions of 2-imino-2H-chromene-3-carboxamides with different dinucleophiles. Full article
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Open AccessArticle
Synthesis of New Bis-Alkylated Phosphono Alkenyl Acyclonucleosides : (Z) and (E)-Diethyl-2-(3-alkyl pyrimidin-1-yl)ethylen-1-yl Phosphonate
Molecules 2000, 5(10), 1139-1145; https://doi.org/10.3390/51001139 - 31 Oct 2000
Cited by 8 | Viewed by 5421
Abstract
The E- and Z- phosphonoalkenyl acyclonucleosides of uracil and thymine were synthesized under Michael addition conditions. Introduction of an alkyl, alkenyl or alkynyl group at the N-3 position of the pyrimidine moiety was accomplished using potassium carbonate in DMF. Full article
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Open AccessArticle
Application of Flow Thermolysis in Organic Synthesis: Easy Access to α,ω-Bis Thienyl- and Bis Pyrrolyl- Alkanes from Methylene Derivatives of Meldrum's Acid
Molecules 2000, 5(10), 1130-1138; https://doi.org/10.3390/51001130 - 31 Oct 2000
Cited by 5 | Viewed by 4447
Abstract
Thermal decomposition of Meldrum's acid derivatives and rearrangement of (alkylsulfanyl) or (propargylamino)methylene ketene intermediates leads in one step to bis thienyl- or bis pyrrolyl-alkanes. Full article
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Open AccessArticle
Studies On Some Acid Divalent-Metal Nitrilotriacetate Complexes
Molecules 2000, 5(10), 1121-1129; https://doi.org/10.3390/51001121 - 31 Oct 2000
Cited by 43 | Viewed by 6261
Abstract
IR and 1H-NMR studies on nitrilotriacetic acid (H3NTA) suggest that the acid exists in the zwitterion form, which allows the existence of intermolecular hydrogen bonding. A tetrahedral structure is established for eleven (1:1) anhydrous acid-metal (II) nitrilotriacetates complexes. The ten [...] Read more.
IR and 1H-NMR studies on nitrilotriacetic acid (H3NTA) suggest that the acid exists in the zwitterion form, which allows the existence of intermolecular hydrogen bonding. A tetrahedral structure is established for eleven (1:1) anhydrous acid-metal (II) nitrilotriacetates complexes. The ten Dq values for the colored complexes were determined spectrophotometrically. The pKa values for the eleven acid metal complexes [M(HNTA)].(OH2)3] were determined and compared with the corresponding pKa values of the [M(OH2)n]+2 ions and also with the log β1 values of the corresponding [M(NTA)]- complexes. X-ray diffraction studies on the ligand and on eight of these complexes are described. Full article
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Open AccessArticle
Crystal Structure of Methyl 4-amino-4-cyano-4,6-dideoxy-2,3-O-isopropylidene-α-L-talopyranoside
Molecules 2000, 5(10), 1113-1120; https://doi.org/10.3390/51001113 - 31 Oct 2000
Cited by 1 | Viewed by 3810
Abstract
The structure of methyl 4-amino-4-cyano-4,6-dideoxy-2,3-O-isopropylidene-α-Ltalopyranoside was established by X-ray analysis confirming a talo configuration at C-4 and suggesting a 1C4 conformation of the pyranose ring. The values of relevant torsion angles and calculated puckering parameters revealed a distortion into [...] Read more.
The structure of methyl 4-amino-4-cyano-4,6-dideoxy-2,3-O-isopropylidene-α-Ltalopyranoside was established by X-ray analysis confirming a talo configuration at C-4 and suggesting a 1C4 conformation of the pyranose ring. The values of relevant torsion angles and calculated puckering parameters revealed a distortion into the direction of 5E conformation, thus indicating a flattening at C-2. Full article
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Open AccessArticle
Synthesis of Novel 1-Substituted and 1,9-Disubstituted-1,2,3,4-tetrahydro-9H-Carbazole Derivatives as Potential Anticancer Agents
Molecules 2000, 5(10), 1101-1112; https://doi.org/10.3390/51001101 - 31 Oct 2000
Cited by 10 | Viewed by 6592
Abstract
Condensation of 1-acetyl-1,2,3,4-tetrahydro-9H-carbazole (2) with some amino compounds furnished the corresponding imino derivatives 3a-e. Compound 3a reacted with chloroacetic acid and underwent cyclization to give the thiazolidine derivative 5. Also, treatment of 3c with thionyl chloride caused cyclization to yield the [1,2,6]thiadiazino derivative [...] Read more.
Condensation of 1-acetyl-1,2,3,4-tetrahydro-9H-carbazole (2) with some amino compounds furnished the corresponding imino derivatives 3a-e. Compound 3a reacted with chloroacetic acid and underwent cyclization to give the thiazolidine derivative 5. Also, treatment of 3c with thionyl chloride caused cyclization to yield the [1,2,6]thiadiazino derivative 6, which gave the corresponding N-formyl derivative 7 upon heating with ethyl formate. In addition, interaction of 3d with ethyl cyanoacetate yielded the monoamide of malonic acid derivative 8. Acylation of carbazole 1 with succinoyl chloride or phenylacetyl choride produced the corresponding azepine (11) and 1,9-diphenyl acetyl derivatives (14), respectively. Compounds 11, 14 were further reacted to give the carbazole derivatives 12, 13 and 15a,b. The cytotoxic activity for some of the prepared compounds against breast cancer B20 is discussed. Full article
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Open AccessArticle
Synthesis of Regioselectively Protected Protocatechuic Acid Derivatives by Biomimetic Transformation of Quinic Acid
Molecules 2000, 5(10), 1094-1100; https://doi.org/10.3390/51001094 - 31 Oct 2000
Cited by 1 | Viewed by 6141
Abstract
3- and 4-monoesterified protocatechuic acid methyl ester (5 and 7 respectively) have been synthesised from quinic acid by a high yields biomimetic rearrangement. Full article
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Open AccessArticle
Synthesis and Reactions of Substituted 3-amino-2-furyl(aryl)-thieno[2,3-b]pyridines
Molecules 2000, 5(10), 1085-1093; https://doi.org/10.3390/51001085 - 31 Oct 2000
Cited by 14 | Viewed by 5384
Abstract
New substituted thieno[2,3-b]pyridines which contain 4-nitropehnyl and 5-nitro-, carboxy-, methoxycarbonyl-2-furyl groups in the 2 position have been obtained. Full article
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Open AccessArticle
Interaction of 1,5-Substituted Pyrrolin-2-ones with Dichlorocarbene under Phase Transfer Catalysis Conditions
Molecules 2000, 5(10), 1082-1084; https://doi.org/10.3390/51001082 - 31 Oct 2000
Cited by 3 | Viewed by 5431
Abstract
Treatment of 5-alkyl(aryl)-3H-pyrrolin-2-ones with dichlorocarbene under phase transfer catalysis conditions at 20-30ºC results in a cycloaddition of the carbene to the C=C bond followed by skeletal rearrangement. Full article
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Open AccessCommentary
Free Access or Free Publication
Molecules 2000, 5(10), 1080-1081; https://doi.org/10.3390/51001080 - 13 Oct 2000
Viewed by 3597
Abstract
Since its inception Molecules has been published on the Internet under a policy of providing "free subscription" based access, limited lately to the current issue, with archival access only provided to paid subscribers.[...] Full article
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