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Synthesis of 5‐aryl and 5‐amidocamptothecins
Author(s) -
Meruva Suresh Babu,
Raghunadh A.,
Anil Kumar N.,
Syam Kumar U. K.,
Vasu Dev R.,
Dubey P. K.
Publication year - 2011
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.590
Subject(s) - chemistry , camptothecin , iminium , ritter reaction , aryl , diastereomer , nucleophile , yield (engineering) , organic chemistry , medicinal chemistry , alkyl , ion , catalysis , materials science , metallurgy
A variety of 5‐aryl‐(20 S )‐camptothecin derivatives were synthesized by the reaction of 5‐hydroxy‐(20 S )‐camptothecin with aromatic hydrocarbons under Friedel‐Craft reaction conditions in moderate to good yield as diastereomeric pairs. The methodology was then extended for the synthesis of 5‐amido‐(20 S )‐camptothecin derivatives by reacting 5‐hydroxy‐(20 S )‐camptothecin with alkyl and aryl nitriles under Ritter type reaction conditions. The reaction is presumed to proceed through an iminium ion intermediate under Friedel Craft and Ritter type reaction condition, which is further trapped by nucleophile present in the reaction medium. J. Heterocyclic Chem., 00 , 00 (2011).