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ChemInform Abstract: Diels-Alder Reaction of 2-Amino-Substituted Furans as a Method for Preparing Substituted Anilines.

✍ Scribed by A. PADWA; M. DIMITROFF; A. G. WATERSON; T. WU


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

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✦ Synopsis


Diels-Alder Reaction of 2-Amino-Substituted Furans as a Method for Preparing Substituted Anilines.

-2-Amino substituted furans react with various dienophiles to intermediate (4 + 2) cycloadducts with high regioselectivity. The electron-withdrawing group is directed in all cases ortho to the amino group. Aromatization of the cycloadducts proceeds either under treatment with BF3 or immediately. The nitro derivative (VII) affords with ketone (IIc) additionally to the expected cycloadduct (VIII) the migration products (IX) and (X). The mild reaction conditions of cycloaddition of carbamate (XII) with maleimide (IId) allow for the isolation of the initial oxybridged product (XIII). -(


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