Crystallization-Induced Diastereomeric Transformation of <i>N</i>-2′-<i>t</i>-Butyl-6′-iodobenzoyl-3-bromocarbazole
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- Kayama Susumu
- School of Pharma Sciences, Teikyo University
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- Tani Norihiko
- School of Pharma Sciences, Teikyo University
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- Takahashi Yuka
- School of Pharma Sciences, Teikyo University
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- Tabata Hidetsugu
- School of Pharma Sciences, Teikyo University
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- Wakamatsu Shintaro
- School of Pharma Sciences, Teikyo University
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- Oshitari Tetsuta
- School of Pharma Sciences, Teikyo University
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- Natsugari Hideaki
- School of Pharma Sciences, Teikyo University
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- Takahashi Hideyo
- School of Pharma Sciences, Teikyo University
Bibliographic Information
- Other Title
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- Crystallization-Induced Diastereomeric Transformation of N-2'-t-Butyl-6'-iodobenzoyl-3-bromocarbazole
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Abstract
We previously reported the atropisomeric properties of 2′-t-butyl-6′-iodo-substituted N-benzoyl-3-bromocarbazole, i.e., the steric or electronic effects of the substituents restricted the rotation about the N–C7′ and C7′–C1′ bonds to separate four stereoisomers (cis/trans for the N–C7′ axis, aR/aS for the C7′–C1′ axis). Furthermore, the 2′-t-butyl-6′-iodo-substituted N-benzoyl 3-bromocarbazole was confirmed to be a gear molecule, in which the rotation about the C7′–C1′ bond was in perfect concert with that about the N–C7′ bond. Herein, we report a unique crystallization-induced diastereomeric transformation found in this molecule. In the isolation process, where the product is recrystallized from the diastereoisomeric mixture, in situ isomerization and selective crystallization could lead to a diastereomeric transformation, and a mixture of diastereomers (trans/cis=54 : 46) was converted to trans-isomer-enriched crystals (trans/cis>96 : 4) in 95% yield. Conformational analysis clarified the preference for the trans versus cis isomer.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 62 (8), 836-838, 2014
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390001204177575168
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- NII Article ID
- 130004677392
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- NII Book ID
- AA00602100
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- COI
- 1:STN:280:DC%2BC2cbos1Cqtw%3D%3D
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 025610000
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- PubMed
- 25087637
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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