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https://doi.org/10.37358/Rev.Chim.1949

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Revista de Chimie (Rev. Chim.), Year 2011, Volume 62, Issue 1,



Constantin Tanase, Miron Teodor Caproiu, Constantin Draghici, Florea G. Cocu, Cristian Enache, Gina Manda

Benzoate Group Migration in Mitsunobu Reaction of N3-benzoyl-5-fluorouracil with Benzoic acid, 2-chloro-5-hydroxy-bicyclo<2.2.1>hept-7-ylmethyl Ester

Abstract:

By Mitsunobu reaction of N3-benzoyl 5-fluorouracil with 2-chloro-5-hydroxy-bicyclo[2.2.1]hept-7-ylmethyl benzoate no nucleoside was obtained. Instead nucleoside we observed a benzoate group migration with the formation of bis-benzoylated compound (5). The structure of this compound was proved by MS, IR, 1H- and 13C-NMR (with complementary COSY and HETCOR spectra), and also by synthesis of the compound by benzoylation of the starting intermediate (1).
Keywords:
Mitsunobu synthesis; N3-benzoyl 5-fluorouracil; 2-chloro-5-hydroxy-bicyclo<2.2.1>hept-7-ylmethyl benzoate; bicyclo<2.2.1> heptane; benzoate group migration

Issue: 2011, Volume 62, Issue 1
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