A new, convenient, highly selective free-radical hydroxymethylation of heteroaromatic bases by persulfate oxidation of ethylene glycol and glycerol, catalysed by AgNO3

Synlett

Volumn , Issue 5, 2004, Pages 874-876

  Minisci, Francesco ^a   Porta, Ombretta ^a   Recupero, Francesco ^a   Punta, Carlo ^a   Gambarotti, Cristian ^a   Pruna, Barbara ^a   Pierini, Monica ^a   Fontana, Francesca ^b  

^a POLITECNICO DI MILANO   (Italy)

^b UNIVERSITY OF BERGAMO   (Italy)

Author keywords

Diols; Free radicals; Heterocycles; Hydroxymethylation; Persulfate

Indexed keywords

AROMATIC COMPOUND; ETHYLENE GLYCOL; FREE RADICAL; GLYCEROL; SILVER NITRATE; SULFATE;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; METHYLATION; OXIDATION; PROTON TRANSPORT;

EID: 1942425153     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-820013     Document Type: Article

References (17)

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2. Reviews on the subject: (a) Minisci, F.; Porta, O. In Advances in Heterocyclic Chemistry, Vol. 16; Katritzky, A. R., Ed.; Academic Press: New York, 1974, 123-180. (b) Minisci, F. Top. Curr. Chem. 1976, 62, 1. (c) Minisci, F.; Fontana, F.; Vismara, E. J. Heterocycl. Chem. 1990, 27, 79.
3. Reviews on the subject: (a) Minisci, F.; Porta, O. In Advances in Heterocyclic Chemistry, Vol. 16; Katritzky, A. R., Ed.; Academic Press: New York, 1974, 123-180. (b) Minisci, F. Top. Curr. Chem. 1976, 62, 1. (c) Minisci, F.; Fontana, F.; Vismara, E. J. Heterocycl. Chem. 1990, 27, 79.
4. Reviews on the subject: (a) Minisci, F.; Porta, O. In Advances in Heterocyclic Chemistry, Vol. 16; Katritzky, A. R., Ed.; Academic Press: New York, 1974, 123-180. (b) Minisci, F. Top. Curr. Chem. 1976, 62, 1. (c) Minisci, F.; Fontana, F.; Vismara, E. J. Heterocycl. Chem. 1990, 27, 79.
5. Recent publications: (a) Cowden, C. J. Org. Lett. 2003, 5, 4497. (b) Minisci, F.; Recupero, F.; Punta, C.; Gambarotti, C.; Pedulli, G. F.; Fontana, F. Chem. Commun. 2002, 2496. (c) Minisci, F.; Recupero, F.; Cecchetto, A.; Punta, C.; Gambarotti, C.; Pedulli, G. P.; Fontana, F. J. Heterocycl. Chem. 2003, 40, 325.
6. Recent publications: (a) Cowden, C. J. Org. Lett. 2003, 5, 4497. (b) Minisci, F.; Recupero, F.; Punta, C.; Gambarotti, C.; Pedulli, G. F.; Fontana, F. Chem. Commun. 2002, 2496. (c) Minisci, F.; Recupero, F.; Cecchetto, A.; Punta, C.; Gambarotti, C.; Pedulli, G. P.; Fontana, F. J. Heterocycl. Chem. 2003, 40, 325.
7. Recent publications: (a) Cowden, C. J. Org. Lett. 2003, 5, 4497. (b) Minisci, F.; Recupero, F.; Punta, C.; Gambarotti, C.; Pedulli, G. F.; Fontana, F. Chem. Commun. 2002, 2496. (c) Minisci, F.; Recupero, F.; Cecchetto, A.; Punta, C.; Gambarotti, C.; Pedulli, G. P.; Fontana, F. J. Heterocycl. Chem. 2003, 40, 325.
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17. 2 solution was evaporated and the residue gave, by flash chromatography (hexane-EtOAc, 2:1) pure 2-hydroxymethyllepidine (17.1 mmol), identified by comparison with an authentic sample. The results in the Table 1 refer to GC analyses.