A novel method for the synthesis of 2,3-benzo-1,3a,6a-triazapentalenes through Pummerer-type reactions of gamma-(benzotriazol-1-yl)allylic sulfoxides
- Authors
- Kim, T; Kim, K; Park, Y
- Issue Date
- Feb-2002
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- betaines; electrophilic additions; epoxidations; heterocycles
- Citation
- EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v.2002, no.3, pp 493 - 502
- Pages
- 10
- Journal Title
- EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 2002
- Number
- 3
- Start Page
- 493
- End Page
- 502
- URI
- https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/16440
- DOI
- 10.1002/1099-0690(20022)2002:3<493::AID-EJOC493>3.0.CO;2-B
- ISSN
- 1434-193X
1099-0690
- Abstract
- Treatment of 1-(arylmethyl)benzotriazoles 1 with nBuLi in THF at -78 degreesC, followed by addition of 1-aryl-2-chloroethanones, gave diastereomeric mixtures of 1-[(aryl)(benzotriazol-1-yl)methyl]oxiranes 2. Treatment of 2 with nBuLi in THF at -78 degreesC, followed by acidification, afforded a mixture of (E)- and (Z)-allylic alcohols 3, which were converted into 1,2-disubstituted 2-(alkyl- or aryl)-t-(benzotriazol-1-yl)-3-sulfanylpropenes 5 via the corresponding allylic chlorides 4. Oxidation of sulfides 5 by mCPBA in CH2Cl2 at room temperature, followed by treatment with trifluoroacetic anhydride (TFAA) at room temperature, gave the title compounds in good yields. It was found that treatment of the title compounds with Raney-Ni in EtOH under hydrogen at reflux gave 2- (pyrazol-1-yl) aniline derivatives in excellent yields.
- Files in This Item
- There are no files associated with this item.
- Appears in
Collections - 이과대학 > 화학과 > 1. Journal Articles
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.