15569-85-4Relevant articles and documents
Thioanalogues of N-1-methylanabasine and nicotine - Synthesis and structure
Wojciechowska-Nowak, Marzena,Boczoń, W?adys?aw,Warzajtis, Beata,Rychlewska, Urszula,Jasiewicz, Beata
, p. 51 - 59 (2011)
The synthesis, spectral characteristics and structures of N-1-methyl-6-(pyridin-3-yl)piperidine-2-thione (1) (thioanalogue of N-1-methylanabasine) and N-1-methyl-(5-pyridin-3-yl)pyrrolidine-2-thione (2) (thioanalogue of nicotine) are reported. Both compounds were obtained using Lawesson's reagent. The structures of compounds 1 and 2 are confirmed by NMR, IR, UV and mass spectroscopy, as well as, by X-ray diffraction analysis. Pyridine ring of compound 1 adopts a pseudo-axial orientation in solution, as well as in a solid state. A substantial lengthening of the C=S bond in the crystals of 1 is interpreted as a sign of an enhanced electron delocalization within the thiolactam group due to the presence of several C-H groups in the nearest vicinity of the sulfur atom. In the crystals of 2, which differ from 1 in that the relatively puckered piperidine-2-thione moiety is replaced by the flat pyrrolidine-2-thione ring, no short CH?S(=C) contacts are observed. Instead, the packing is governed by stacking interactions between pyridine rings. The pyrrolidine and pyridine rings in 2 are nearly perpendicular to each other and the pyrrolidine moiety adopts a flattened half-chair conformation.
Preparation method of artificially synthesized nicotine
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, (2019/10/04)
The invention discloses a preparation method of artificially synthesized nicotine, and belongs to the technical field of chemical synthesis. According to the synthesis method of a racemate (+/-)-(R,S)-nicotine and a natural optical active enantiomer (-)-(S)-nicotine, nicotinate and diester of succinic acid (or N-alkyl succinimide) are taken as the primary raw materials; and defects of a conventional nicotine synthesis technology such as difficulty for massive production, high cost, and the like, are overcome. Specifically, the provided synthesis method has the advantages that the primary raw materials are easily available, the preparation technology is simple, the cost is low, the prepared nicotine does not contain any other harmful tobacco compound, and the preparation method is suitable for industrial large-scale production.
Sp3 C-H Arylation and Alkylation Enabled by the Synergy of Triplet Excited Ketones and Nickel Catalysts
Shen, Yangyang,Gu, Yiting,Martin, Ruben
supporting information, p. 12200 - 12209 (2018/09/27)
Triplet ketone sensitizers are of central importance within the realm of photochemical transformations. Although the radical-type character of triplet excited states of diaryl ketones suggests the viability for triggering hydrogen-atom transfer (HAT) and single-electron transfer (SET) processes, among others, their use as multifaceted catalysts in C-C bond-formation via sp3 C-H functionalization of alkane feedstocks still remains rather unexplored. Herein, we unlock a modular photochemical platform for forging C(sp3)-C(sp2) and C(sp3)-C(sp3) linkages from abundant alkane sp3 C-H bonds as functional handles using the synergy between nickel catalysts and simple, cheap and modular diaryl ketones. This method is distinguished by its wide scope that is obtained from cheap catalysts and starting precursors, thus complementing existing inner-sphere C-H functionalization protocols or recent photoredox scenarios based on iridium polypyridyl complexes. Additionally, such a platform provides a new strategy for streamlining the synthesis of complex molecules with high levels of predictable site-selectivity and preparative utility. Mechanistic experiments suggest that sp3 C-H abstraction occurs via HAT from the ketone triplet excited state. We believe this study will contribute to a more systematic utilization of triplet excited ketones as catalysts in metallaphotoredox scenarios.
