New Reactions of 3‐Vinyl‐ and 3‐(2‐Propenyl)Indoles with  N ‐Phenylmaleimide: [4 + 2] Cycloaddition, ene reaction, and dimerization | Zendy

Pfeuffer Ludwig | Zendy; Pindur Ulf | Zendy

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New Reactions of 3‐Vinyl‐ and 3‐(2‐Propenyl)Indoles with N ‐Phenylmaleimide: [4 + 2] Cycloaddition, ene reaction, and dimerization

Author(s) -

Pfeuffer Ludwig,

Pindur Ulf

Publication year - 1988

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19880710220

Subject(s) - chemistry , ene reaction , stereospecificity , cycloaddition , lewis acids and bases , propenyl , medicinal chemistry , catalysis , organic chemistry , stereochemistry

Depending on the substitution pattern of the aminobutadiene subunit in the selected 3‐vinylindoles 1, 3, 6 , and 9 , stereospecific [4 + 2] cycloadditions (‘ endo ’‐preference) and dimerizations take place on reaction with N ‐phenylmaleimide. In the reaction of 9 with N ‐phenylmaleimide in the absence of a Lewis ‐acid catalyst, a competing ene reaction occurs in addition to the Diels ‐ Alder reaction.

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