Gregorio Torres’s research while affiliated with University of Malaga and other places

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Publications (15)


ChemInform Abstract: Multicomponent C-Alkylation Reactions of Aromatic Aldimines with Trialkylboranes Reagents
  • Article

August 2010

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40 Reads

ChemInform

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Carmen Munoz

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Rafael Suau

ChemInform Abstract: The Photo-Fries Rearrangement of 2,5-Disubstituted Phenyl Acetates

June 2010

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11 Reads

ChemInform

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.



Multicomponent C‐Alkylation Reactions of Aromatic Aldimines with Trialkylboranes Reagents

April 2010

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50 Reads

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11 Citations

The one-pot three-component reaction of an aryl aldehyde, an arylamine, and a trialkylborane in the presence of hydrogen peroxide afforded the alkylated arylamines 1 in good yields via oxidized imine–borane complexes. In addition, the versatility of our procedure has been confirmed by the use of enolizable aldehydes, alkylic amines, and cyclic imines.



ChemInform Abstract: Organoborane Reagents in the C-Alkylation of Aromatic Aldimines.

January 2008

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35 Reads

ChemInform

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.


Organoborane Reagents in theC-Alkylation of Aromatic Aldimines

September 2007

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44 Reads

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8 Citations

The reaction of an aldimine with dicyclohexylboron chloride in the presence of hydrogen peroxide gives N-[cyclohexyl(aryl)methyl]arylamines 2 in good yields via oxidized imine–borane complexes. The amines can also be obtained by a three-component reaction involving an arenecarbaldehyde, an arylamine and a dialkylchloroborane reagent. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)


From Berbines to Protopines: Regiocontrolled Hofmann Elimination/Hydroboration/Oxidation of N‐Substituted Berbinium Salts

February 2006

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77 Reads

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4 Citations

An improved synthetic approach to protopines based on the sequential Hofmann elimination, hydroboration and oxidation of N-(arylmethyl)berbinium salts has been designed. By using berberine chloride as the starting material, this sequence of reactions has provided two new nonnatural protopines, N-benzyl-N-nordihydroallocriptopine and N-(p-methoxybenzyl)-N-nordihydroallocriptopine and the natural allocriptopine. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)


Identification and quantification of isoquinoline alkaloids in the genusSarcocapnos by GC-MS

September 2005

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73 Reads

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11 Citations

Phytochemical Analysis

Six cularine alkaloids, cularicine, O-methylcularicine, celtisine, cularidine, cularine and celtine, three isocularine alkaloids, sarcophylline, sarcocapnine and sarcocapnidine, and five non-cularine alkaloids, glaucine, protopine, ribasine, dihydrosanguinarine and chelidonine, were identified and quantified by GC-MS in nine taxa of the genus Sarcocapnos (Fumariaceae). The chemotaxonomic significance of the results is discussed. Copyright © 2005 John Wiley & Sons, Ltd.


Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS

September 2005

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249 Reads

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19 Citations

Phytochemical Analysis

Six cularine alkaloids, cularicine, O-methylcularicine, celtisine, cularidine, cularine and celtine, three isocularine alkaloids, sarcophylline, sarcocapnine and sarcocapnidine, and five non-cularine alkaloids, glaucine, protopine, ribasine, dihydrosanguinarine and chelidonine, were identified and quantified by GC-MS in nine taxa of the genus Sarcocapnos (Fumariaceae). The chemotaxonomic significance of the results is discussed.


Citations (9)


... Wu et al. identified and quantified the intracellular concentration of protopine in HL-7702 cells by liquid chromatography-tandem mass spectrometry (LC-MS/MS) [14]. Protopine can also be identified and quantified by GC-MS and TLC/GC-MS methods [15,16]. Compared to HPLC-MS or HPLC-NMR, TLC/GC-MS has the advantages of short identification time, low cost of separation, and simple operation. ...

Reference:

Identification and Quantification, Metabolism and Pharmacokinetics, Pharmacological Activities, and Botanical Preparations of Protopine: A Review
Identification and quantification of isoquinoline alkaloids in the genusSarcocapnos by GC-MS
  • Citing Article
  • September 2005

Phytochemical Analysis

... In contrast with other related alkaloids that contain the quinolizidine moiety (e.g. berbines), 25 inversion at the N bridgehead of the starting material is unlikely in phenanthroquinolizidines and the adjacent methyl group should stabilize the trans isomer. It is generally assumed that, either by formation of an iminium ion or via recombination of radical pairs in the solvent-cage, 26 the Stevens rearrangement is suprafacial. ...

From protopines to berbines: Synthesis of 1-methoxystylopine and its N-metho salts from coulteropine
  • Citing Article
  • June 2002

Tetrahedron

... Establishment of the requisite cis-diol 146 from this transformation was attributed to the chelation of cationic samarium with the two carbonyl functionality before the coupling took place. The synthesis of (+)-alopecuridineÁTFA (147) was completed in another three steps from 146, and the synthetic (+)-alopecuridine could be converted to (+)-sieboldine A (139) Using 157 as a starting material, the total synthesis of (À)-farnesiferol C was accomplished in 7 steps. ...

Total Synthesis of New 8-(Arylmethyl)berbines
  • Citing Article
  • February 2010

... To appraise the applicability of the procedure, we extended the study of the one-pot alkylation reaction to enantiomerically pure amines. Chiral amines (1S)-1-phenylethanamine (13) and L-valine methyl ester (14) were made to react with p-anisaldehyde (12) and Et 3 B (Scheme 4), in dichloromethane at 20°C. ...

Multicomponent C‐Alkylation Reactions of Aromatic Aldimines with Trialkylboranes Reagents
  • Citing Article
  • April 2010

... Recently, Cabedo et al. 118 To explore the role of the 1-benzyl group in the tetrahydroisoquinolines, Andreu et al. 119 prepared compounds with a cyclohexylmethyl group at the C-1 position to replace the benzyl substituent (115a,b, 116; Figure 9). These novel compounds, like their benzyl congeners, retained substantial D 2 receptor binding. ...

Syntheses of dopaminergic 1-cyclohexylmethyl-7,8-dioxygenated tetrahydroisoquinolines by selective heterogeneous tandem hydrogenation
  • Citing Article
  • Full-text available
  • December 2002

Tetrahedron

... The total synthesis of these alkaloids typically involves isoquinoline synthesis methods, such as Bischler-Napieralski cyclization, 6) Pictet-Spengler cyclization, 7,8) intramolecular N-alkylation, 6) intramolecular hydroamination, 7) and others. [9][10][11][12] Alternative synthetic approaches include Stevens rearrangement for the installation of C8-substituents. 13) The relative stereochemistry between H8 and H14 is trans in javaberine A (1), theoneberine (2), and O-methylcorytenchirine (3), whereas a cis relationship is observed in coralydine (4). ...

Regio‐ and Stereoselective Stevens Rearrangement of Benzyltetrahydroprotoberberinium Salts
  • Citing Article
  • November 2004

... The family Fumariaceae is composed of about 600 species from worldwide spread genera Fumaria, Corydalis, Rupicapnos, Sarcocapnos, Ceratocapnos and Platycapnos [1,2,3,4]. Genus Corydalis is represented by 470 plant species [4,5]. This genus comprises only four taxa in Bulgaria (Corydalis solida (L.) Swartz., C. marschalliana (Willd.) ...

Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS
  • Citing Article
  • September 2005

Phytochemical Analysis