First Synthesis of 2‐Vinylindole and its  diels‐Alder  Reactions with CC‐Dienophiles | Zendy

Pindur Ulf | Zendy; Eitel Manfred | Zendy

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First Synthesis of 2‐Vinylindole and its diels‐Alder Reactions with CC‐Dienophiles

Author(s) -

Pindur Ulf,

Eitel Manfred

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.19880710517

Subject(s) - chemistry , dimethyl acetylenedicarboxylate , cycloaddition , intramolecular force , wittig reaction , carbazole , diels–alder reaction , yield (engineering) , indole test , medicinal chemistry , diene , stereochemistry , organic chemistry , catalysis , materials science , natural rubber , metallurgy

By means of an intramolecular Wittig process, 2‐vinylindole ( 2 ) was prepared. The indole 2 functions as a heterocyclic, donor‐activated 1,3‐diene and undergoes [4+2] cycloaddition reactions with dimethyl acetylenedicarboxylate, N ‐phenylmaleimide, and p ‐benzoquinone leading to the novel carbazole dervatives 3 , 4 , 5c , 6 and 7 respectively. The reaction of 2 with acceptor (A)‐Substituted dienophiles ( e.g. ) ACHCH 2 , AC≡(CH) does not yield products that can be isolated.

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