ONE-STEP SYNTHESIS OF DIALKYNYL-1,2-DIONES AND THEIR CONVERSION TO FUSED PYRAZINES BEARING ENEDIYNE UNITS

Authors
FAUST R WEBER C FIANDANESE V MARCHESE G PUNZI A
Citation
R. Faust et al., ONE-STEP SYNTHESIS OF DIALKYNYL-1,2-DIONES AND THEIR CONVERSION TO FUSED PYRAZINES BEARING ENEDIYNE UNITS, Tetrahedron, 53(43), 1997, pp. 14655-14670
Citations number
50
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
43
Year of publication
1997
Pages
14655 - 14670
Database
ISI
SICI code
0040-4020(1997)53:43<14655:OSODAT>2.0.ZU;2-Z
Abstract
A convenient procedure for the preparation of symmetrically end-protec ted dialkynyl-1,2-diones 3 from lithium acetylides and oxalyl chloride in the presence of CuBr and LiBr is described. The condensation of 3 with various aromatic and heteroaromatic 1,2-diamines leads to pyrazin e-based alpha-dialkynylated heterocycles. The enediyne substructure of diethynylquinoxaline can be thermally rearranged in a Bergman cycliza tion reaction. (C) 1997 Elsevier Science Ltd.