synthesis of pyrimidine-containing 3-aminobutenolides

2004 Nucleic acids U 0700 Synthesis of Pyrimidine-Containing 3-Aminobutenolides. — Starting from isox- azolines (I), obtained by 1,3-dipolar cycloaddition, two competitive reaction routes leading either to pyrimidine-containing 3-aminobutenolides (II) or to homo-N,O nucleosides (IV). The former pathway based on removal of the hydrogen atom at C-3 with a basic reagent (TBAF) and subsequent ring opening followed by intramolecular acyl substitution. The latter pathway based on reduction of the ester group at C-3 affording (IV). — (CHIACCHIO, U.; IANNAZZO*, D.; PIPERNO, A.; PISTARA, V.; RESCIFINA, A.; ROMEO, G.; ROMEO, R.; Tetrahedron 60 (2004) 31, 6593-6596; Dip. Farm.-Chim., Univ. Messina, I-98168 Messina, Italy; Eng.) — Bartels 47- 193

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Page 1: Synthesis of Pyrimidine-Containing 3-Aminobutenolides

2004

Nucleic acidsU 0700 Synthesis of Pyrimidine-Containing 3-Aminobutenolides. — Starting from isox-

azolines (I), obtained by 1,3-dipolar cycloaddition, two competitive reaction routes leading either to pyrimidine-containing 3-aminobutenolides (II) or to homo-N,O nu-cleosides (IV). The former pathway based on removal of the hydrogen atom at C-3 with a basic reagent (TBAF) and subsequent ring opening followed by intramolecular acyl substitution. The latter pathway based on reduction of the ester group at C-3 affording (IV). — (CHIACCHIO, U.; IANNAZZO*, D.; PIPERNO, A.; PISTARA, V.; RESCIFINA, A.; ROMEO, G.; ROMEO, R.; Tetrahedron 60 (2004) 31, 6593-6596; Dip. Farm.-Chim., Univ. Messina, I-98168 Messina, Italy; Eng.) — Bartels

47- 193

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