Edward C. Taylor, Joseph L. Pont and John C. Warner, heterodienophilic intramolecular diels-alder reactions of 1,2,4-triazines. Synthesis of novel poly: Tetrahedron 43, 5159-5168 (1987)

• Book ID: 104205258
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 30 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)90328-x

✦ Synopsis

Diels-Alder Reactions of 1,2&Triazines. Synthesis of Novel Polycyclic Condensed Pyrazines and Lumaxines, Tetruhedron 43, 5159-5168 (1987). The following paragraph was inadvertently omitted from the above manuscript; it should appear at the end of page 5159 and before the beginning of the text on page 5162.

1.3~Dimethyl-7-hydroxy&azalumazine (!I) was smoothly converted to the corresponding 7-chloro derivative 6 with phosphorus oxychloride. l1 Nucleophilic displacement of chloride ion with sodium Zqanophenoxide afforded 1,3-dimethyl-7-(2'qanophenoxy)&azaIumazine ( 7) in excellent yield. Compound 7 underwent intramolecular cycoladdition in refhtxing nitrobenzene over the course of 2 weeks to yield the condensed lumazine 8 in modest yield (Scheme 1).