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Grignard Reagents and Their N ‐analogues in the Synthesis of Tricyclic and Tetracyclic Cage‐like Lactams
Author(s) -
Tkachenko Igor V.,
Tarabara Igor N.,
Omelchenko Irina V.,
Palchykov Vitalii A.
Publication year - 2018
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.3302
Subject(s) - chemistry , tricyclic , tetrahydrofuran , stereochemistry , ether , lithium (medication) , bicyclic molecule , reagent , inhibitory postsynaptic potential , lactam , stereoselectivity , combinatorial chemistry , organic chemistry , catalysis , medicine , neuroscience , solvent , biology , endocrinology
A convenient method is reported for the synthesis of 34 novel tricyclic and tetracyclic cage‐like lactams in high to excellent yields. The method involves treatment of easily available exo ‐2,3‐epoxy(or Ts‐aziridino)bicyclo[2.2.1]heptan‐ endo ‐5,6‐dicarboximides by Grignard reagents, their N ‐analogues, or phenyl lithium in tetrahydrofuran. In silico screening of biological activity spectrum showed high probability levels of glyceryl‐ether monooxygenase inhibitory, testosterone 17β‐dehydrogenase (NADP+) inhibitory, bilirubin oxidase inhibitory, and anti‐ischemic activity for tetracyclic derivatives.