2020年2月7日
Cycloamination strategies for renewable N-heterocycles
Green Chemistry
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- 巻
- 22
- 号
- 3
- 開始ページ
- 582
- 終了ページ
- 611
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1039/c9gc03655e
- 出版者・発行元
- ROYAL SOC CHEMISTRY
© 2020 The Royal Society of Chemistry. Biomass resources have infinite possibilities for introducing nitrogen, sulfur, or phosphorus heteroatoms into their structures by virtue of controllable carbon-heteroatom bond formation. In this review, cycloamination approaches for thermal (catalyst-free) and catalytic transformation of biomass feedstocks into N-heterocyclic molecules including mechanistic pathways are analyzed. Bottom-up (small molecule substrates) and top-down (large molecule substrates) are considered. Sustainable routes for synthesis of five-membered (pyrroles, pyrrolidones, pyrazoles, imidazoles), six-membered (pyridines, pyrazines), fused (indoles, benzimidazoles), and other relevant azaheterocycles are critically assessed. Production of biomass-derived six-, seven-, and eight-membered as well as fused N-heterocyclic compounds with present approaches have relatively low selectivities. Attention to methods for forming analogous sulfur or phosphorus heteroatom compounds from biomass resources using either bottom-up or top-down strategies appear to have been greatly overlooked. Synthetic auxiliaries (heating modes, nitrogen sources) that enhance reaction efficiency and tunability of N-heterocyclic ring size/type are considered and plausible reaction mechanisms for pivotal pathways are developed.
- リンク情報
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- DOI
- https://doi.org/10.1039/c9gc03655e
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000523465000001&DestApp=WOS_CPL
- Scopus
- https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85079695174&origin=inward 本文へのリンクあり
- Scopus Citedby
- https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85079695174&origin=inward
- ID情報
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- DOI : 10.1039/c9gc03655e
- ISSN : 1463-9262
- eISSN : 1463-9270
- SCOPUS ID : 85079695174
- Web of Science ID : WOS:000523465000001