Cycloamination strategies for renewable N-heterocycles

Hu Li, Haixin Guo, Zhen Fang, Taku Aida, Richard Lee Smith

Research output: Contribution to journalReview article

6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)582-611
Number of pages30
JournalGreen Chemistry
Volume22
Issue number3
DOIs
Publication statusPublished - 2020 Feb 7

ASJC Scopus subject areas

  • Environmental Chemistry
  • Pollution

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