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ChemInform Abstract: A Simple Synthesis of N-Acetyl-1,4-dihydropyrano(3,4-b)indol-3-one: Evidence for a Stepwise Ionic Pathway in the Generation of Indole-2,3- quinodimethanes.

✍ Scribed by O. M. JAKIWCZYK; K. E. NIELSEN; H. NANDIN DE CARVALHO; G. I. DMITRIENKO

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Evidence for a Stepwise Ionic Pathway in the Generation of Indole-2,3-quinodimethanes.

-A strategy employing C-2 carbon substitution of (I) by NBS bromination is used for an effective synthesis of the lactone (IV). However, contrary to the previously reported analogues (V) compound (IV) is totally inert to thermal decarboxylation. This suggests together with the fact that the reaction is accelerated by polar solvents that the decarboxylation is an ionic process.

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