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2005
Fused pyridine derivatives
R 0450
Intramolecular Inverse-Electron-Demand Diels—Alder Reactions of Imidazoles
1,2,4-Triazines: A New Route to 1,2,3,4-Tetrahydro-1,5-naphthyridines and
07- 137 with
Related Heterocycles. — Triazines of type (V) and (VII) readily undergo intramolecular Diels—Alder reaction under thermal or microwave conditions. The expected fused
deazapurine derivatives are not obtained. Instead tetrahydro-1,5-naphthyridines like
(VI) and (IX) are formed which result from N2 and nitrile elimination. Prolonged heating leads to aromatized products such as (VII). Starting from tetramethylene homologues like (X) pyridoacepines are available. In some cases trace amounts of the desired
products (XII) are observed. — (LAHUE, B. R.; LO, S.-M.; WAN, Z.-K.; WOO, G. H.
C.; SNYDER*, J. K.; J. Org. Chem. 69 (2004) 21, 7171-7182; Dep. Chem., Boston
Univ., Boston, MA 02215, USA; Eng.) — Jannicke
2005
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