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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.