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A simple route for the synthesis of novel norcantharimide derivatives via acidolysis with hydrochloric acid (gas)
Author(s) -
Köse Aytekin
Publication year - 2021
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.4248
Subject(s) - chemistry , hydrochloric acid , stereospecificity , organic chemistry , ethyl chloroacetate , catalysis , hydrate
In this work, seven new norcantharimide derivatives were synthesized by an acidolysis method. The compounds were prepared by acidolyzing trans ‐1,4‐diacetate and trans ‐1,2‐chloroacetate structures, which were obtained by stereospecific cleavage of the internal etheric bond of the tricyclic imides. The HCl (gas) was produced from the reaction of H 2 SO 4 with NaCl. The resulting gas was bubbled into the reaction mixture. Trans ‐1,4‐diacetate and trans ‐1,2‐chloroacetate were thus acidolyzed, and the corresponding diol and halohydrin products were obtained respectively in moderate overall yields from low‐cost starting materials, using simple and easily scalable chemistry. The products were characterized by means of spectroscopic techniques. The synthesized compounds have high potential as anticancer agents and can be valuable for studies in this area.

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