Cycloamination strategies for renewable N-heterocycles

被引:120
作者
Li, Hu [1 ]
Guo, Haixin [2 ]
Fang, Zhen [1 ]
Aida, Taku Michael [3 ]
Smith, Richard Lee, Jr. [2 ]
机构
[1] Nanjing Agr Univ, Coll Engn, Biomass Grp, 40 Dianjiangtai Rd, Nanjing 210031, Jiangsu, Peoples R China
[2] Tohoku Univ, Grad Sch Environm Studies, Aoba Ku, 6-6-11 Aoba, Sendai, Miyagi 9808579, Japan
[3] Fukuoka Univ, Fac Engn, Dept Chem Engn, Jonan Ku, 8-19-1 Nanakuma, Fukuoka 8140180, Japan
基金
日本学术振兴会;
关键词
ONE-POT SYNTHESIS; THERMO-CATALYTIC CONVERSION; GAMMA-AMINO ALCOHOLS; LEVULINIC ACID; REDUCTIVE AMINATION; BUILDING-BLOCKS; PYRIDINE BASES; FORMIC-ACID; HYDROTHERMAL LIQUEFACTION; AZOMETHINE YLIDES;
D O I
10.1039/c9gc03655e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:582 / 611
页数:30
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