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Aminomethyl psoralens. Electrophilic substitution of hydroxymethylphthalimide on linear furocoumarins
Author(s) -
Heindel Ned D.,
Choudhuri Mridula,
Ressner Joel,
Foster Natalie
Publication year - 1985
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.5570220119
Subject(s) - chemistry , electrophilic substitution , furocoumarins , furan , electrophile , ring (chemistry) , hydrazine (antidepressant) , substitution (logic) , substitution reaction , cleavage (geology) , nucleophilic substitution , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , photochemistry , catalysis , geotechnical engineering , chromatography , fracture (geology) , computer science , engineering , programming language
A new synthetic route to aminomethylpsoralens, substituted on the furan‐ring, has been developed by electrophilic substitution of N ‐hydroxymethylphthalimide and subsequent hydrazinolysis. Hydroxy and methoxy activating functions on the psoralens lead to multi‐site substitution and the products of these phthalimido‐methylations resist simple cleavage with hydrazine. The two‐step introduction of a single CH 2 NH 2 group is successful in psoralens containing only methyl substituents.