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Thermal Valence Rearrangements of Heterocycles. Part 2. A new synthetic approach towards the indole ring system
Author(s) -
Bennett Grace A.,
Mullen George B.,
Georgiev Vassil St.
Publication year - 1989
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.19890720808
Subject(s) - indole test , chemistry , pyrrole , ring (chemistry) , toluene , yield (engineering) , valence (chemistry) , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy
A new synthetic approach towards the indole ring system is described. When dimethyl 1‐methyl‐2‐oxa‐1‐aza‐spiro[4.5]dec‐3‐ene‐3,4‐dicarboxylate ( 6 ) was refluxed in toluene, the previously known dimethyl 4,5,6,7‐tetra‐hydro‐1‐methyl‐1 H ‐indole‐2,3‐dicarboxylate ( 7 ) was obtained in 71% yield, via a 2,3‐dihydroisoxazole‐pyrrole rearrangement. After treatment with DDQ , the tetrahydro analogue 7 was converted to the corresponding dimethyl 1‐methyl‐1 H ‐indole‐2,3‐dicarboxylate ( 8 ).