The unexpected and efficient direct nucleophilic C-4 hydroxy (oxo) substitution by sodium alkoxides on 2-methoxy- and 2-methylthio-4(3H)-pyrimidinones bearing a diethylamino moiety on the C-6 side chain is reported. An unprecedented tandem C-6 side chain Hofmann-like elimination/C-4 pyrimidinone substitution is also reported. This provides a good method for the synthesis of new C-6 vinyl cytosine derivatives. (C) 1997 Elsevier Science Ltd.

Botta, M., Occhionero, F., Saladino, R., Crestini, C., Nicoletti, R. (1997). An unexpected and efficient direct nucleophilic C-4 hydroxy substitution on 2-methoxy- and 2-methylthio-4(3H)-pyrimidinones bearing a diethylamino moiety on the C-6 side chain. TETRAHEDRON LETTERS, 38(47), 8249-8252 [10.1016/S0040-4039(97)10159-9].

An unexpected and efficient direct nucleophilic C-4 hydroxy substitution on 2-methoxy- and 2-methylthio-4(3H)-pyrimidinones bearing a diethylamino moiety on the C-6 side chain

CRESTINI, CLAUDIA;
1997-01-01

Abstract

The unexpected and efficient direct nucleophilic C-4 hydroxy (oxo) substitution by sodium alkoxides on 2-methoxy- and 2-methylthio-4(3H)-pyrimidinones bearing a diethylamino moiety on the C-6 side chain is reported. An unprecedented tandem C-6 side chain Hofmann-like elimination/C-4 pyrimidinone substitution is also reported. This provides a good method for the synthesis of new C-6 vinyl cytosine derivatives. (C) 1997 Elsevier Science Ltd.
1997
Pubblicato
Rilevanza internazionale
Articolo
Sì, ma tipo non specificato
Settore CHIM/03 - CHIMICA GENERALE E INORGANICA
English
Con Impact Factor ISI
Botta, M., Occhionero, F., Saladino, R., Crestini, C., Nicoletti, R. (1997). An unexpected and efficient direct nucleophilic C-4 hydroxy substitution on 2-methoxy- and 2-methylthio-4(3H)-pyrimidinones bearing a diethylamino moiety on the C-6 side chain. TETRAHEDRON LETTERS, 38(47), 8249-8252 [10.1016/S0040-4039(97)10159-9].
Botta, M; Occhionero, F; Saladino, R; Crestini, C; Nicoletti, R
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/52121
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