New reactivity of hydroxyallylpyridyl derivatives as C-3 carbon nucleophiles

Tetrahedron Letters

Volumn 45, Issue 10, 2004, Pages 2113-2115

  Giomi, Donatella ^a   Piacenti, Michela ^a   Brandi, Alberto ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Heterocyclic electrophiles; Hydroxyallylpyridyl derivatives; Nucleophilic substitution; Picoline derivatives; Thermal reactions

Indexed keywords

ALCOHOL; HYDROGEN; PYRIDINE DERIVATIVE;

ACIDITY; ARTICLE; ATOM; CHEMICAL REACTION KINETICS; THERMODYNAMICS;

EID: 1242317876     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.049     Document Type: Article

References (11)

1. Uff B.C. Boulton A.J., McKillop A. Comprehensive Heterocyclic Chemistry. Vol. 2:1984;329-335 Pergamon, Oxford, UK.
2. Dennis N. McKillop A. Comprehensive Heterocyclic Chemistry II. Vol. 5:1996;101-104 Pergamon, Oxford, UK.
3. Cicchi S., Cordero F.M., Giomi D. Prog. Heterocycl. Chem. 15:2003;261.
4. Uenishi J., Hiraoka T., Hata S., Nishiwaki K., Yonemitsu O. J. Org. Chem. 63:1998;2481.
5. Sato N., Narita N. Synthesis. 2001;1551.
6. The same conversion was observed by heating 1a at 70 °C for three days.
7. For the synthesis of 1b in enantiopure form, see Ref. 3.
8. Uenishi J., Hiraoka T., Yuyama K., Yonemitsu O. Heterocycles. 52:2000;719.
9. The reported yields were determined on the basis of the recovered starting material.
10. For examples of 4,5-dicyanopyridazine ( 13 ) acting as an electrophile, see: Giomi D., Cecchi M. Tetrahedron. 58:2002;8067.
11. Giomi D., Cecchi M. J. Org. Chem. 68:2003;3340.