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Duran, F.J.; Ghini, A.A.; Dauban, P.; Dodd, R.H.; Burton, G. "Synthesis of 6,19-sulfamidate bridged pregnanes" (2005) Journal of Organic Chemistry. 70(21):8613-8616
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Abstract:

Conformationally restrained substituted pregnane-20-one derivatives were obtained by an intramolecular nitrene addition onto a C-5/C-6 double bond involving a tethered C-19 sulfamoyl moiety. The resulting aziridine underwent regioselective nucleophilic ring opening at C-5 at room temperature with cyanide, fluoride, and acetate. In the isolated case of acetate, a reversal of regioselectivity was observed at higher temperatures, a result attributed to a rearrangement process involving aziridine ring opening at the C-5 position and subsequent migration of the acetyl meiety to C-6. © 2005 American Chemical Society.

Registro:

Documento: Artículo
Título:Synthesis of 6,19-sulfamidate bridged pregnanes
Autor:Duran, F.J.; Ghini, A.A.; Dauban, P.; Dodd, R.H.; Burton, G.
Filiación:Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina
Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, F-91198 Gif-sur-Yvette Cedex, France
Palabras clave:Addition reactions; Conformations; Ring opening polymerization; Stereochemistry; Substitution reactions; Sulfur compounds; 6,9-sulfamidate bridged pregnanes; Nitrene; Nucleophilic ring opening; Regioselectivity; Aromatic compounds; 4 aminobutyric acid A receptor; acetic acid; aziridine derivative; cyanide; fluoride; neurosteroid; pregnane derivative; sulfanilamide; anticonvulsant activity; article; chemical reaction; conformational transition; derivatization; molecular interaction; reaction analysis; ring opening; solubility; synthesis; Bridged Compounds; Molecular Structure; Pregnanes; Sulfonic Acids
Año:2005
Volumen:70
Número:21
Página de inicio:8613
Página de fin:8616
DOI: http://dx.doi.org/10.1021/jo051290a
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:acetic acid, 127-08-2, 127-09-3, 64-19-7, 71-50-1; cyanide, 57-12-5; fluoride, 16984-48-8; sulfanilamide, 34612-79-8, 6101-31-1, 63-74-1; Bridged Compounds; Pregnanes; Sulfonic Acids
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v70_n21_p8613_Duran

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Citas:

---------- APA ----------
Duran, F.J., Ghini, A.A., Dauban, P., Dodd, R.H. & Burton, G. (2005) . Synthesis of 6,19-sulfamidate bridged pregnanes. Journal of Organic Chemistry, 70(21), 8613-8616.
http://dx.doi.org/10.1021/jo051290a
---------- CHICAGO ----------
Duran, F.J., Ghini, A.A., Dauban, P., Dodd, R.H., Burton, G. "Synthesis of 6,19-sulfamidate bridged pregnanes" . Journal of Organic Chemistry 70, no. 21 (2005) : 8613-8616.
http://dx.doi.org/10.1021/jo051290a
---------- MLA ----------
Duran, F.J., Ghini, A.A., Dauban, P., Dodd, R.H., Burton, G. "Synthesis of 6,19-sulfamidate bridged pregnanes" . Journal of Organic Chemistry, vol. 70, no. 21, 2005, pp. 8613-8616.
http://dx.doi.org/10.1021/jo051290a
---------- VANCOUVER ----------
Duran, F.J., Ghini, A.A., Dauban, P., Dodd, R.H., Burton, G. Synthesis of 6,19-sulfamidate bridged pregnanes. J. Org. Chem. 2005;70(21):8613-8616.
http://dx.doi.org/10.1021/jo051290a