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Palladium(0)‐Catalyzed CarbonHydrogen Bond Functionalization for the Synthesis of Indoloquinazolinones
Author(s) -
Tsukano Chihiro,
Okuno Masataka,
Nishiguchi Hiromi,
Takemoto Yoshiji
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400078
Subject(s) - chemistry , regioselectivity , palladium , substituent , surface modification , ring (chemistry) , catalysis , combinatorial chemistry , yield (engineering) , pharmacophore , methylene , hydrogen bond , functional group , stereochemistry , organic chemistry , molecule , materials science , polymer , metallurgy
The indoloquinazolinone ring system has attracted considerable attention as a pharmacophore, because it shows various biological activities. The reported synthetic methods for the compound are simple and direct, but are not effective for the direct synthesis of indoloquinazolinone with a methylene group at the C‐6 position. A palladium(0)‐catalyzed cyclization of chloroquinazolinone via CH functionalization was developed for a concise synthesis of indoloquinazolinone derivatives. The presence of a substituent at the C‐6 position is important for obtaining the product in good yield. The conformation of the reaction intermediate, in particular the NCPd bond angle, is important for the regioselectivity of the reaction.