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Papers by alberto jerezano
ChemInform, Feb 5, 2013
ABSTRACT An efficient synthetic approach for the construction of the 1-oxygenated carbazole core ... more ABSTRACT An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.
Synthesis, Aug 23, 2012
List of Contents (1) 1 H and 13 C Spectra of New Compounds S2-S23 1 H NMR (300 MHz, CDCl 3) Spect... more List of Contents (1) 1 H and 13 C Spectra of New Compounds S2-S23 1 H NMR (300 MHz, CDCl 3) Spectrum of 11c. 13 C NMR (75.4 MHz, CDCl 3) Spectrum of 11c. 1 H NMR (300 MHz, CDCl 3) Spectrum of 11d. 13 C NMR (75.4 MHz, CDCl 3) Spectrum of 11d. 1 H NMR (300 MHz, CDCl 3) Spectrum of 11e. 13 C NMR (75.4 MHz, CDCl 3) Spectrum of 11e.
ChemInform, Feb 21, 2014
The title reaction is catalyzed by magnesium bromide and carried out under solvent-free conditions.
ChemInform, May 26, 2011
A New Approach for Construction of Quaternary Chiral Centers: Preparation of α-Branched Serine De... more A New Approach for Construction of Quaternary Chiral Centers: Preparation of α-Branched Serine Derivatives.-Michael addition of α,β-unsaturated carbonyl compounds [cf. (II)] or nitroolefins like (IV) to the pyrrolooxazole proceeds with good regio-and diastereoselectivity in the presence of Lewis acids to furnish the corresponding 7a-alkylated pyrrolooxazoles in good yields. In most cases, the anti-adducts are obtained predominantly. These adducts are smoothly transformed to the title α-branched serine derivatives by reductive removal of the nitro group, cis-dihydroxylation and oxidative pyrrolidone ring opening. Oxidation of the formyl group and oxazole ring hydrolysis provides access to the target quaternary serine derivatives [cf.
ChemInform, Apr 4, 2013
A one‐pot procedure including Ugi three‐component reaction, aza‐Diels—Alder cycloaddition and aro... more A one‐pot procedure including Ugi three‐component reaction, aza‐Diels—Alder cycloaddition and aromatization provides key intermediates (V).
![Research paper thumbnail of ChemInform Abstract: Efficient Synthetic Approach to Substituted Benzo[b]furans and Benzo[b]thiophenes by Iodine-Promoted Cyclization of Enaminones](https://attachments.academia-assets.com/110260590/thumbnails/1.jpg)
](ChemInform, Dec 22, 2014
An efficient synthetic approach to the substituted benzo[b]furan and benzo[b]thiophene scaffolds ... more An efficient synthetic approach to the substituted benzo[b]furan and benzo[b]thiophene scaffolds by iodine-mediated cyclization of the corresponding enaminones is described. This protocol was applied to a large series of these latter precursors to afford the respective benzoheterocycles substituted at the C-2 position by a carbonyl group functionality. A study of the factors that control this process reveals that the reactivity depends on the presence of electron-donor groups in the aryl ring of the aryloxycarbonylic and arylthiocarbonylic moieties.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones
Synlett, 2012
ABSTRACT A series of nuevamine aza-analogues were prepared in moderate to good yields in two reac... more ABSTRACT A series of nuevamine aza-analogues were prepared in moderate to good yields in two reaction steps. The synthetic strategy involves an isonitrile-based multicomponent reaction, including an aza-Diels-Alder cycloaddition and Pictet-Spengler reaction as postcondensation.
The Journal of Organic Chemistry, 2013
A highly efficient and regioselective synthesis of 1,2-dihydroquinolines via a multicomponent rea... more A highly efficient and regioselective synthesis of 1,2-dihydroquinolines via a multicomponent reaction between an aniline and two ketones is described. This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substituted anilines and nonsymmetrically substituted ketones, principally a single product was found among the four expected regioisomers. A variety of anilines and ketones, including cyclic ketones, were evaluated providing a series of 1,2-dihydroquinolines with diverse substitution patterns. A study of the mechanism is discussed. There is evidence of the in situ formation of the imine as a result of the reaction between the aniline and one of the ketones, before annulation to the heterocyclic ring.
Helvetica Chimica Acta, 2011
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
ChemInform, Feb 21, 2014
The title reaction is catalyzed by magnesium bromide and carried out under solvent-free conditions.
Arkivoc, 2013
The synthesis of 2-carbonylindoles was achieved via a iodine-mediated cyclization of the correspo... more The synthesis of 2-carbonylindoles was achieved via a iodine-mediated cyclization of the corresponding enaminone precursors, which were formed by reaction of the -arylaminomethylene carbonyl derivatives with N,N′-dimethylformamide dimethyl acetal (DMFDMA). An alternative and more efficient procedure consisted of a similar cyclization of the enaminones, but under solvent-free and grinding reaction conditions. In another iodine-promoted procedure, 2carbonyl-3-dimethylaminoindoles were synthesized via a one-pot cascade reaction between the -arylaminomethylene carbonyl derivative and DMFDMA.
ChemInform, 2013
ABSTRACT An efficient synthetic approach for the construction of the 1-oxygenated carbazole core ... more ABSTRACT An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.
ChemInform, Feb 5, 2013
ABSTRACT An efficient synthetic approach for the construction of the 1-oxygenated carbazole core ... more ABSTRACT An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.
Synthesis, Aug 23, 2012
List of Contents (1) 1 H and 13 C Spectra of New Compounds S2-S23 1 H NMR (300 MHz, CDCl 3) Spect... more List of Contents (1) 1 H and 13 C Spectra of New Compounds S2-S23 1 H NMR (300 MHz, CDCl 3) Spectrum of 11c. 13 C NMR (75.4 MHz, CDCl 3) Spectrum of 11c. 1 H NMR (300 MHz, CDCl 3) Spectrum of 11d. 13 C NMR (75.4 MHz, CDCl 3) Spectrum of 11d. 1 H NMR (300 MHz, CDCl 3) Spectrum of 11e. 13 C NMR (75.4 MHz, CDCl 3) Spectrum of 11e.
ChemInform, Feb 21, 2014
The title reaction is catalyzed by magnesium bromide and carried out under solvent-free conditions.
ChemInform, May 26, 2011
A New Approach for Construction of Quaternary Chiral Centers: Preparation of α-Branched Serine De... more A New Approach for Construction of Quaternary Chiral Centers: Preparation of α-Branched Serine Derivatives.-Michael addition of α,β-unsaturated carbonyl compounds [cf. (II)] or nitroolefins like (IV) to the pyrrolooxazole proceeds with good regio-and diastereoselectivity in the presence of Lewis acids to furnish the corresponding 7a-alkylated pyrrolooxazoles in good yields. In most cases, the anti-adducts are obtained predominantly. These adducts are smoothly transformed to the title α-branched serine derivatives by reductive removal of the nitro group, cis-dihydroxylation and oxidative pyrrolidone ring opening. Oxidation of the formyl group and oxazole ring hydrolysis provides access to the target quaternary serine derivatives [cf.
ChemInform, Apr 4, 2013
A one‐pot procedure including Ugi three‐component reaction, aza‐Diels—Alder cycloaddition and aro... more A one‐pot procedure including Ugi three‐component reaction, aza‐Diels—Alder cycloaddition and aromatization provides key intermediates (V).
ChemInform, Dec 22, 2014
An efficient synthetic approach to the substituted benzo[b]furan and benzo[b]thiophene scaffolds ... more An efficient synthetic approach to the substituted benzo[b]furan and benzo[b]thiophene scaffolds by iodine-mediated cyclization of the corresponding enaminones is described. This protocol was applied to a large series of these latter precursors to afford the respective benzoheterocycles substituted at the C-2 position by a carbonyl group functionality. A study of the factors that control this process reveals that the reactivity depends on the presence of electron-donor groups in the aryl ring of the aryloxycarbonylic and arylthiocarbonylic moieties.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones
Synlett, 2012
ABSTRACT A series of nuevamine aza-analogues were prepared in moderate to good yields in two reac... more ABSTRACT A series of nuevamine aza-analogues were prepared in moderate to good yields in two reaction steps. The synthetic strategy involves an isonitrile-based multicomponent reaction, including an aza-Diels-Alder cycloaddition and Pictet-Spengler reaction as postcondensation.
The Journal of Organic Chemistry, 2013
A highly efficient and regioselective synthesis of 1,2-dihydroquinolines via a multicomponent rea... more A highly efficient and regioselective synthesis of 1,2-dihydroquinolines via a multicomponent reaction between an aniline and two ketones is described. This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substituted anilines and nonsymmetrically substituted ketones, principally a single product was found among the four expected regioisomers. A variety of anilines and ketones, including cyclic ketones, were evaluated providing a series of 1,2-dihydroquinolines with diverse substitution patterns. A study of the mechanism is discussed. There is evidence of the in situ formation of the imine as a result of the reaction between the aniline and one of the ketones, before annulation to the heterocyclic ring.
Helvetica Chimica Acta, 2011
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
ChemInform, Feb 21, 2014
The title reaction is catalyzed by magnesium bromide and carried out under solvent-free conditions.
Arkivoc, 2013
The synthesis of 2-carbonylindoles was achieved via a iodine-mediated cyclization of the correspo... more The synthesis of 2-carbonylindoles was achieved via a iodine-mediated cyclization of the corresponding enaminone precursors, which were formed by reaction of the -arylaminomethylene carbonyl derivatives with N,N′-dimethylformamide dimethyl acetal (DMFDMA). An alternative and more efficient procedure consisted of a similar cyclization of the enaminones, but under solvent-free and grinding reaction conditions. In another iodine-promoted procedure, 2carbonyl-3-dimethylaminoindoles were synthesized via a one-pot cascade reaction between the -arylaminomethylene carbonyl derivative and DMFDMA.
ChemInform, 2013
ABSTRACT An efficient synthetic approach for the construction of the 1-oxygenated carbazole core ... more ABSTRACT An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.