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Reduction of the indole ring system: synthesis of 4,5,6,7-tetrahydroindoles

โœ Scribed by Casey C. McComas; David L. Van Vranken

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
250 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A general two-step procedure for the reduction of indoles to the corresponding 4,5,6,7-tetrahydroindoles has been developed. A regioselective Birch reduction followed by catalytic hydrogenation is employed to accomplish this transformation. Yields for the sensitive pyrrole products are typically between 40 and 50%. This method provides access to complex chiral pyrroles that cannot be readily prepared by other methods.

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The 3-alkyl-4,5,6,7\_tetrahydroindoles 4a and 4b reacted with -lead tetraacetate in acetic acid to give the corresponding 7acetoxy derivatives; hydrolysis, followed by treatment with potassium ferricyanide in refluxing acetic acid afforded the novel porphyrins 6a and 6b. --Recently o variety of nick