Allylic nitration of 3β-sitosterol and cholesterol acetate: Preparation of 7-nitro derivatives

Steroids

Volumn 62, Issue 6, 1997, Pages 500-503

  Jiménez Estrada, Manuel ^a   García, M Olivia ^c   Navarro, Arturo O ^a   Eusebio, José L ^a   Alvarez, Cecilio T ^a   Penieres, Guillermo C ^c   Gutiérrez, René P ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b Lab de Quim Teor   (Mexico)

^c NONE

Author keywords

3 sitosterol and cholesterol 7 nitro derivative; Acetate; HNO3 bentonite

Indexed keywords

1,4 DIHYDROPYRIDINE; ACETIC ACID; CHOLESTEROL; SITOSTEROL;

ARTICLE; CHOLESTEROL METABOLISM; ENERGY RESOURCE; INFRARED RADIATION; NITRATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; RADIATION; STRUCTURE ACTIVITY RELATION;

CHOLESTEROL ESTERS; HEAT; INFRARED RAYS; MICROWAVES; NITRATES; SITOSTEROLS;

EID: 0242709601     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(97)00021-4     Document Type: Article

References (15)

1. Bull JR, Jones ERH, Meakins GD (1965). Nitro-steroids. Part II. A new route to nitro-steroids. J Chem Soc pp. 2601-2614.
2. Fieser LF, Fieser M (1959). Steroids. Reinhold, New York, Ch 43-44.
3. Windaus A (1920). Uber einige umwandlungs produkte des Cholestens und Pseudo-Cholestens und uber den nachweiseiner der doppelbindung benachbarten methylengruppe im Cholesterin. Chem Ber 36:488-497.
4. Topchiev AV (1959). Nitration of Hydr roons and other Organic Compounds. Pergamon, London, 199-209.
5. Anagnostopoulos CE, Fieser LF (1954). Nitration of unsaturated steroids. J Am Chem Soc 76:532-536.
6. Laszlo P (1987). Preparative Chemistry Using Supported Reagents. Academic Press, New York, Ch 1.
7. 3/bentonite et irradiation aux micro-ondes. Tetrahedron Lett 34:623-625.
8. 2/bentonite: A new reagent for the oxidation of Hantzsch's dihydropyridines using microwave irradiation in the absence of solvent (1). Synth Comm 21:619-624.
9. 2/bentonite using microwave irradiation in the absence of solvent (II). Synth Comm 21:2137-2141.
10. Cabrera C, Vázquez D, Velasco L, Salmon M, Arias JL (1992). 1,3-Dioxolane formation with a montmorillonite-type clay catalyst. J Mol Catal 75:101-107.
11. Kaufmann S (1964). Steroids CCLI. Lead tetraacetate oxidation of 17β-hydroxy-5α-androst-len-3-one acetate. J Org Chem 29: 1348-1350.
12. Pool GC, Teuben S (1987). In: Wayda AL, Darensbourg MY (eds), IR Radiation as Heat Source in Vacuum Sublimation in Practical Organometallic Chemistry, Vol. 357, ACS Symposium Series, ACS, Washington, DC, pp. 30-33.
13. Bergström S, Wintersteiner O (1941). Autoxidation of sterols in colloidal aqueous solution. The nature of the products formed from cholesterol. J Biol Chem 141:597-610.
14. Gigante B, Prazers AO, Marcelo-Curto MJ, Cornélis A, Laszlo P (1995). Mild and selective nitration by "claycop." J Org Chem 60:3445-3447.
15. Buncel E, Bourns AN (1960). The mechanism of the carbonyl elimination reaction of benzyl nitrate. Can J Chem 38:2457-2466.