Reactions of 7-(Methoxyimino)-4-methyl-2H-chromene-2,8(7H)-dione with Phosphorus Ylides. Synthesis of 2-Substituted 6-Methyl-8H-benzopyrano[7,8-d]oxazol-8-ones

7‐(Methoxyimino)‐4‐methyl‐2H‐chromene‐2,8(7H)‐dione (3) reacts with phosphonium salts 1a–c, 8a, b under phasetransfer catalysis conditions to afford the title 2‐substituted 6‐methylbenzopyranooxazol‐8‐ones 5a–c, 10a, b, respectively, along with compound 6, instead of the expected Wittig reaction pro...

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Veröffentlicht in:Liebigs Annalen der Chemie 1993-11, Vol.1993 (11), p.1175-1177
Hauptverfasser: Bezergiannidou-Balouctsi, Catherine, Litians, Konstantions E., Malamidou-Xenikaki, Elizabeth, Nicolaides, Demetrios N.
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Sprache:eng
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Zusammenfassung:7‐(Methoxyimino)‐4‐methyl‐2H‐chromene‐2,8(7H)‐dione (3) reacts with phosphonium salts 1a–c, 8a, b under phasetransfer catalysis conditions to afford the title 2‐substituted 6‐methylbenzopyranooxazol‐8‐ones 5a–c, 10a, b, respectively, along with compound 6, instead of the expected Wittig reaction products. However, the reaction of 3 with the stable phosphorus ylides 11a–c in addition to the corresponding benzopyranooxazoles 12a–c and compound 6 affords in the last case compound 16 as well according to a sequence involving an initial Wittig reaction between 11c and 3.
ISSN:0170-2041
1099-0690
DOI:10.1002/jlac.1993199301190