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A New Method for the Preparation of Intermediates for 2,6‐Substituted Anthrapyridazones
Author(s) -
Cybulski Marcin,
Sidoryk Katarzyna,
Formela Adam,
Michalak Olga,
Rosa Anna,
Mróz Katarzyna,
Maruszak Wioleta
Publication year - 2017
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.2738
Subject(s) - chemistry , permanganate , reagent , periodate , anthraquinones , alkylation , combinatorial chemistry , organic chemistry , catalysis , botany , biology
A new method for the preparation of 2‐substituted 6‐chloro‐2,7‐dihydro‐3 H ‐dibenzo[ de , h ]cynnoline‐3,7‐diones has been developed. The compounds have been obtained in an original three‐step procedure comprising the oxidation of 1‐methyl‐9,10‐anthraquinones with periodate or permanganate/brominating reagent systems, cyclization to 6‐chloro‐2,7‐dihydro‐3 H ‐dibenzo[ de , h ]cynnoline‐3,7‐dione, and selective alkylation thereof. The selected processes were applied in the efficient scale‐up of specific 2,6‐substituted 2,7‐dihydro‐3 H ‐dibenz[ de , h ]cinnolin‐3,7‐dione derivatives, currently being investigated pre‐clinically as anticancer agents.