Radical Cyclization in Heterocycle Synthesis 15. Relationship between a Radical Species and Radical Acceptors of Three Different Types of Double Bond in Radical Addition-Cyclization
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- Miyata Okiko
- Kobe Pharmaceutical University, Motoyamakita
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- Kajisa Seiko
- Kobe Pharmaceutical University, Motoyamakita
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- Ueda Masafumi
- Kobe Pharmaceutical University, Motoyamakita
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- Yamauchi Masashige
- Department of Pharmaceutical Sciences, Josai University
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- Naito Takeaki
- Kobe Pharmaceutical University, Motoyamakita
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Abstract
Relationship between a radical species and radical acceptors of three different types of double bond in radical addition–cyclization was systematically investigated. Substrates carrying α,β-unsaturated amide, isolated olefin, and oxime ether moieties underwent radical addition–cyclization to give differently substituted lactams depending upon the radicals used. The sulfanyl radical addition–cyclization of the substrate proceeded smoothly to give the 5-membered lactam having an alkoxyamino group as a result of preferable addition of an intermediary α-carbonyl radical to the oxime ether. On the other hand, the triethylborane-mediated radical addition-cyclization gave the lactam bearing an iodomethyl group as a result of addition to an intermediary α-carbonyl radical to isolated olefin. The different regioselectivity was explained by the stability of the intermediary radical and the interaction between SOMO and HOMO.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 53 (8), 995-1002, 2005
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390001204171233408
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- NII Article ID
- 10016655997
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 7373085
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- PubMed
- 16079534
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed