IBX-mediated synthesis of indazolone via oxidative N–Nbond formation and unexpected formation of quinazolin-4-one: in situ generation of formaldehyde from dimethoxyethane

Title
IBX-mediated synthesis of indazolone via oxidative N–Nbond formation and unexpected formation of quinazolin-4-one: in situ generation of formaldehyde from dimethoxyethane
Author
이상열
Keywords
Hypervalent iodine; Indazolone; Iodoxybenzoic acid; N–N bond formation; Quinazolin-4-one
Issue Date
2016-03
Publisher
PHARMACEUTICAL SOC KOREA
Citation
ARCHIVES OF PHARMACAL RESEARCH, v. 39, No. 3, Page. 302-309
Abstract
Synthesis of indazolone derivatives, which exhibit diverse biological and pharmaceutical activities, were achieved by hypervalent λ(5) iodine reagents, such as iodoxybenzoic acid (IBX),-mediated oxidative N-N bond forming cyclization. In this study, the equivalence of IBX was optimized to promote the formation of N-N bond by oxidatively generated acylnitrenium ion. Dimethoxyethane and dichloroethane were discovered as alternative solvents and the reaction could be conducted in more concentrated condition. Some unprecedented substrates successfully afforded the corresponding indazolone in new condition discovered in this study. When the reactions were conducted in DME solvent, substrates with no electron-rich phenyl substituted amides afforded the unanticipated quinazolin-4-ones in moderate yields, which were not formed in DCE solvent. The formation of quinazolin-4-ones was attributed to the in situ generation of formaldehyde from DME. Therefore, the reaction might undergo different pathway in DME when the substrate aryl amides have phenyl rings without electron donating substituents.
URI
https://www.ncbi.nlm.nih.gov/pubmed/26780246http://hdl.handle.net/20.500.11754/50769
ISSN
0253-6269
DOI
10.1007/s12272-016-0706-z
Appears in Collections:
RESEARCH INSTITUTE[E](부설연구소) > INSTITUTE OF PHARMACEUTICAL SCIENCE AND TECHNOLOGY(약학기술연구소) > Articles
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