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The schmidt reaction on 3a,4,5,6‐tetrahydrosuccinimido[3,4‐ b ]‐acenaphthen‐10‐one and its alkylated derivatives
Author(s) -
Campaigne E.,
Huffman J. C.,
Yodice Richard
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180127
Subject(s) - chemistry , isoquinoline , alkylation , schmidt reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The rearrangement of 3a,4,5,6‐tetrahydrosuccinimido[3,4‐ b ]acenaphthen‐10‐one and two methylated derivatives using Schmidt conditions is described. The ratio of the major product, 2,3,8,9‐tetrahydro‐3‐oxo‐1 H ‐benz[ de ]isoquinoline‐1,9a‐(7 H )dicarboximide, to the minor product, 2,3,6,7‐tetrahydro‐3‐oxo‐4 H ‐benz[ ij ]‐isoquinoline‐4,4a‐(5 H )dicarboximide, under different acidic conditions is given. The ratios of analogous products from the methylated derivatives are similar under similar conditions.